5-Bromo-2-fluorobenzaldehyde → HCID 43160375, compound

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask was charged with 2-fluoro-5-bromobenzaldehyde (1.01 g) and tetrahydrofuran (50 mL), placed under a nitrogen atmosphere then cooled to −78° C. To this solution was added a 1M solution of phenylmagnesium bromide (5 mL). The reaction was stirred for 15 min then removed from the cold bath and allowed to warm to 0° C. Quenching was achieved by the addition of water and diethyl ether. The organic layer was collected, dried over magnesium sulfate then concentrated to an oil. The residue was dissolved in methylene chloride (100 mL) and treated with Dess-Martin periodinane (2.12 g) at room temperature. The reaction mixture was stirred for 30 min then loaded directly onto a silica gel pad. The pad was eluted with methylene chloride, and the desired fractions were combined and concentrated to dryness to provide (5-bromo-2-fluorophenyl)(phenyl)methanone as a yellow oil (0.80 g). 1H NMR (400 MHz, DMSO-D6) δ ppm 7.8 (m, 1 H) 7.7 (m, 3 H) 7.6 (m, 1 H) 7.5 (m, 2 H) 7.3 (m, 1 H)

Provenance & Evidence