5-Bromo-2-fluorobenzaldehyde → HCID 54595143, compound
Reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[CH:4]=[O:5].[C:11]1([Mg]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1>[Br:10][C:7]1[CH:8]=[CH:9][C:2]([F:1])=[C:3]([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:5])[CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
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. Purification using silica gel chromatography provided (5-bromo-2-fluorophenyl)(phenyl)methanol as a colorless oil. H1 NMR (d6-dmso): 7.68 (dd, 1H), 7.46 (m, 1H), 7.32 (m, 4H), 7.23 (m, 1H), 7.12 (dd, 1H), 6.16 (d, 1H), 5.89 (d, 1H).