(3,4-Difluorophenyl)acetic acid → HCID 21187692, compound

Participants

Reaction Steps

A solution of 3,4-difluorophenylacetic acid (2.9 g, 16.8 mmol) in 80 mL dry THF was cooled to −78° C. and treated with LDA (2.0 M heptane/THF/ethylbenzene, 42 mmol, 21 mL) for 15 minutes. Then cyclopropylcarboxaldehyde (17 mmol, 1.27 mL, 1.19 g) was added via syringe and the reaction warmed slowly to room temperature over 1 hr. The reaction mixture was diluted with 5% aqueous potassium hydrogen sulfate (50 mL), and extracted with ethyl acetate (2×150 mL). The combined extracts were dried (Na2SO4), filtered and concentrated in vacuo. The lower rf material crystallized to give 1.4 g of solid. 1H NMR (CDCl3, 300 MHz) δ 7.40-7.00 (m, 3H, Ar—H), 3.75-3.60 (br m, 1H), 3.50-3.40 (m, 1H), 0.95-0.70 (m, 1H), 0.5-0.20 (m, 4H).

Provenance & Evidence