Hydrochloric Acid → (4-Bromo-2-methoxyphenyl)(4-fluorophenyl)methanone

Participants

Reaction Steps

To a suspension of AlCl3 (14.7 g, 110 mmol) in 250 mL of 1,2-dichloroethane was added 4-fluorobenzoyl chloride (11.8 mL, 100 mmol) at rt. The resulting mixture was stirred at rt for 15 min. and 3-bromoanisole (16.8 g, 90.0 mmol) in 20 mL of 1,2-dichloroethane was added. After 1 h at rt, the brown solution was poured into ice. 2N HCl was added to the aqueous layer followed by an extraction with CH2Cl2. The combined organics were dried (MgSO4), filtered and concentrated. The residue was subjected to chromatography on silica gel (EtOAc/hexane 5:95 to 7:93) affording 5.1 g of a solid that was triturated with 20 mL of EtOAc/hexane (10:90). The title compound was obtained from filtration, and additional product was recovered from the mother liquors.

Provenance & Evidence