1-Bromo-3-chloropropane → 4'-Chloro-4-chloropropoxybenzophenone

Participants

Reaction Steps

To a suspension of sodium hydride (60%, 1.7 g, 43 mmol) in dimethylformamide (200 mL) was added 4'-chloro-4-hydroxybenzophenone (5 g, 22 mmol) portionwise. The mixture was stirred at room temperature for 2 hours, then 1-bromo-3-chloropropane (4.4 mL, 43 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction was quenched with methanol (10 mL) and filtered through Celite®. The filtrate was taken up in ether (300 mL), washed thrice with water (150 mL) and dried over sodium sulfate. The solution was concentrated to give 6.1 g (90%) of 4'-chloro-4-chloropropoxybenzophenone as an amber oil. 1H NMR (CDCl3): δ7.98-6.89(m,8H), 4.19(t,2H), 3.85(t,2H), 2.29(m,2H).

Provenance & Evidence