1-((4-Fluorophenyl)carbamoyl)cyclopropane-1-carboxylic acid

A suspension of cyclopropane-1,1-dicarboxylic acid CA1 (10.0 g, 0.08 mol) in THF

(56 mL) was stirred in an ice water bath and triethylamine (7.79 g, 0.08 mol) was added
slowly to keep the reaction temperature below 10 ℃. SOCl2 (9.16 g, 0.08 mol) was added
slowly to the reaction mixture to keep the reaction temperature below 8 ℃. When the
addition was complete, the mixture was stirred below 5 ℃ for another 1 h. 4-Fluoroaniline
SI1 (7.77 g, 0.07 mol) in THF (20 mL) was added to the reaction solution slowly to keep the
reaction temperature below 8 ℃, and stirred on the ice water bath for another 3 h. The
reaction solution was then diluted with ethyl acetate (100 mL) and water (100 mL), stirred at
room temperature for 30 min. The organic phase was separated, washed with water (80 mL)
and brine (80 mL). The solution was concentrated under vacuum to give the solid, dried at 50
℃ for 4 h to give the product CA2 as a cream solid (9.2 g, 92%). 1 H NMR (DMSO-d6): d
1.41 (s, 4H), 7.14 (t, J ¼ 8.8 Hz, 2H), 7.61 (dd, J ¼ 4.8, 8.8 Hz, 2H), 10.57 (s, 1H). Anal:
Calcd for C11H10FNO3 : C; 59:19; H; 4:52: Found : C; 59:30; H; 4:45