Acetaldehyde → HCID 57812530, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of LDA (6 mL, 12 mmol) in THF (10 mL) was added 3-chlorobromobenzene (1.91 g, 9.98 mmol) in THF (5 mL) at −78° C. under nitrogen, the resulting mixture was stirred at −78° C. for 1 h, then a solution of acetaldehyde (0.66 g, 15 mmol) in THF (5 mL) was added. The mixture was slowly warmed to rt. The mixture was quenched with water (10 mL), and diluted with EtOAc (50 mL). The organic phase was separated, washed with brine (10 mL), and dried over anhydrous sodium sulfate. The crude material was purified by silica gel chromatography (Hex:EtOAc=95:5→90:10) to give the title compound as a colorless oil. 1H NMR (CDCl3): δ=1.64 (d, J=6.8 Hz, 3H), 2.98 (d, J=10.4 Hz, 1H, —OH), 5.58 (m, 1H), 7.04 (t, J=8.1 Hz, 1H), 7.31 (dd, J=8.1, 1.2 Hz, 1H), 7.49 (dd, J=8.1, 1.0 Hz, 1H).

Provenance & Evidence