Experiment 5 Suzuki Coupling

Experiment 5: Suzuki Coupling
Experiment 5: Suzuki coupling
Matthew Blake
03/18/23
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https://www.coursehero.com/file/203910603/Experiment-5-Suzuki-Couplingdocx/
Reaction Scheme:
Mechanism:
Reagent Table
Reagent CAS # MW Density MP/BP Amt Equivalents Safety

used
4’- 99-90-1 199.04 1.647 50 0.001mol 0.2g Irritant,

Bromoacetophen g/mol g/ml 0.12mL health
one hazard
Phenylboronic 98-80-6 121.93 1.1 g/mL 216 0.00105 0.128g irritant

Acid g/mol mol 0.11mL
Palladium 1000ppm - 10 gtts Toxic

catalyst solution corrosive
in 5% HCl
Ethanol 64-17-5 46.07 789 kg/L -114.1 25mL 428.15mol Flammab

g/mol 19,725g le
1M KOH 1310-58- 56.11 1.05g/mL 360 2mL 0.37mol Corrosive

3 g/mol 2.1g
Diethyl Ether 60-29-7 74.12 713 kg/L 34.6 5mL 3565g Flammab
g/mol 48.09mol le, irritant
Hexane 110-54-3 86.18 655 kg/L 69 1mL 655g Flammab

g/mol 8.83mol le,
Irritant,
health
hazard
Calculations
Procedure:
1. Dissolve 0.001 mol of 4-bromoacetophenone in 5mL of ethanol in a 25mL flask
2. Add 0.00105mol of Phenylboronic acid and stir until dissolved
a. Make sure to sitr rapidly!
3. Add 10 drops of the palladium catalyst to your reaction mixture followed by 2mL of the
1M KOH solution
4. Stir until solid precipitates from the solution (usually between 5-20 minutes)
5. Stir for an addition 2 minutes
6. Stop sitting after precipitate starts forming
7. After precipitate forms, add 10mL of water to rxn mixture
8. Dry solid for 10 minutes via vacuum filtration
9. Rinse with 1 more mL of water and allow to dry for another 10 minutes
10. Dissolve in 5mL of ether and then add 1mL of hexane
11. Dry solution with sodium sulfate
12. Pipet the clear solvent into a pre-weighed flask
13. Dry with nitrogen for a few minutes to give product
14. Calculate percent yield, obtain TLC, IR, and HNMR
Running the TLC:
When running this reaction, the developing solvent was a 75/25 mixture
of Hexane to ethyl acetate in that order. The results are as follows:
compound Rf value
Solution 5 cm
4-bromoacetophenone 3.3cm/5cm = 0.66
Phenylboronic acid 0.5cm / 5cm = 0.1
Co-spot 0.5/5cm = 0.1
3.3cm/5cm = 0.66
Product 3.3cm/5cm = 0.66
Based on the TLC, it is found that the product may have been made. Its hard to determine
because of the fact that the 4-bromoacetophenone and Product dots seem to be merged into
one another. There is no phenylboronic left in the reaction. It does not appear in the product
lane like the 4-bromoacetophenone does. The fact that this rxn ran to completion, but came out
with an incredibly low yield (0.003g) is not surprising due to the phenylboronic acid being my
limiting reagent in this experiment. However, looking at the Rf values of each of the lanes, it
seems that the 4-bromoacetophenone and product are about the same in polarity (0.66, more
nonpolar than the phenylboronic acid), but again, due to there not being two distinct markers on
the TLC plate, this is only speculation. The IR and HNMR tells me that my product was made,
but it's incredibly difficult to distinguish upon analysis of my TLC plate.
IR
The IR spectrum that was retrieved from class, I have some reservations about. More
specifically about the hydrogen bonding that would be more akin and normally seen in the 3200
- 3600cm-1 range. The IR spectrum from the SDBS website, the Hydrogen bonding is very
apparent while on the one from class is non existent. However, the range of ~1600cm-1 is
consistent with the phenyl rings being shown on both Spectra and that the fingerprint regions in
both spectra are nearly identical. The only major difference between the two is that the point
near ~1600cm-1 on the spectra taken in class is a lot stronger and sharper than the one found
on the SDBS website while some of the points in the fingerprint region are weaker/smaller than
the one found on the SDBS website.
HNMR
Based on the HNMR, even with the disturbance (?) shown on the HNMR retrieved in class, it
still resembles the HNMR found on the SDBS website. There is the large peak that looks to be
around ~7ppm and the small quartet peak thats attached to it. The next peak right next to it also
has the doublet peak around ~8ppm. With it being a quartet in the one ~7ppm, this tells me that
there are several hydrogen atoms that are the same being shielded while the one ~8ppm its
just 2 hydrogens.
Conclusion:
So, with some research and the help of my GSI (Alexander), it was determined that my reaction
had run to completion based off of TLC analysis because the phenylboronic acid had not
appeared in the product lane as it had appeared in the other lanes with an Rf value of 0.1.
However, compared to the theoretical yield of my product (0.2g), it makes sense why my actual
yield is extremely small in comparison to it (0.003g or 1.5% yield). There could only be two
reasons on why this makes sense
1. Due to the smaller amount of Phenylboronic acid that was being used in the reaction and
it being 100% used up
2. Evaporation during drying
Both of these scenarios are likely, but I believe that scenario one is the most likely. The yield
was almost non-existent to be frank. Going back to the HNMR and IR however. Based upon
analysis of the spectra and comparing them to literature found on reaxys and SDBS, there is a
high chance that my product was not pure at all. Once again, going back to the IR spectra, the
noticeable lack of H-bonding on the spectra that I took in comparison to the SBDS is very
apparent. In the HNMR, not only do several other peaks show up (possibly water and the
chloroform used to dilute the sample), but there is a large disturbance (?) that shows along the
X-axis of my spectra that I'm not too sure what it is or why it's there.
References:
IR for product: https://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi
HNMR for product: https://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi
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Experiment 5: Suzuki Coupling

Experiment 5: Suzuki coupling

Reagent CAS # MW Density MP/BP Amt Equivalents Safety

4’- 99-90-1 199.04 1.647 50 0.001mol 0.2g Irritant,

Phenylboronic 98-80-6 121.93 1.1 g/mL 216 0.00105 0.128g irritant

Palladium 1000ppm - 10 gtts Toxic

Ethanol 64-17-5 46.07 789 kg/L -114.1 25mL 428.15mol Flammab

1M KOH 1310-58- 56.11 1.05g/mL 360 2mL 0.37mol Corrosive

Hexane 110-54-3 86.18 655 kg/L 69 1mL 655g Flammab

1. Dissolve 0.001 mol of 4-bromoacetophenone in 5mL of ethanol in a 25mL flask

2. Add 0.00105mol of Phenylboronic acid and stir until dissolved

a. Make sure to sitr rapidly!

5. Stir for an addition 2 minutes

6. Stop sitting after precipitate starts forming

7. After precipitate forms, add 10mL of water to rxn mixture

8. Dry solid for 10 minutes via vacuum filtration

10. Dissolve in 5mL of ether and then add 1mL of hexane

11. Dry solution with sodium sulfate

12. Pipet the clear solvent into a pre-weighed flask

13. Dry with nitrogen for a few minutes to give product

14. Calculate percent yield, obtain TLC, IR, and HNMR

Running the TLC:

of Hexane to ethyl acetate in that order. The results are as follows:

4-bromoacetophenone 3.3cm/5cm = 0.66

Phenylboronic acid 0.5cm / 5cm = 0.1

Co-spot 0.5/5cm = 0.1

Product 3.3cm/5cm = 0.66

but it's incredibly difficult to distinguish upon analysis of my TLC plate.

the one found on the SDBS website.

reasons on why this makes sense

it being 100% used up

2. Evaporation during drying

IR for product: https://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi

HNMR for product: https://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi

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