4-(Chloromethyl)benzoyl chloride → HCID 10502995, compound

Participants

Reaction Steps

To a solution of 4-(chloromethyl)benzoyl chloride (804 mg, 4.26 mmol) in CH2Cl2 (21 mL) was added AlCl3 (850 mg, 6.39 mmol) in a single portion, and the yellow solution was stirred for 15 min at ambient temperature. A solution of 6-(4-fluorophenyl)indole-1-carboxylic acid dimethylamide (1.00 g, 3.55 mmol), prepared as in step 1, in CH2Cl2 was added dropwise and the dark solution was stirred for 2 hours at ambient temperature. Additional AlCl3 (0.24 g, 1.78 mmol) was added and the reaction mixture was stirred for 0.5 hours. The reaction mixture was poured into a separatory funnel containing ice water and CH2Cl2. The layers were separated and the aqueous phase was extracted three times with CH2Cl2. The combined organic layers were washed with saturated aqueous NaHCO3, dried over MgSO4, filtered, and concentrated in vacuo. Pure 6-(4-fluorophenyl)-3-(4 -chloromethylbenzoyl)indole-1-carboxylic acid dimethylamide (294 mg) was obtained by chromatography on silica gel (25%, then 50% ethyl acetate/hexanes).

Provenance & Evidence