Benzyl Bromide → Benzaldehyde, 2-fluoro-3-(phenylmethoxy)-

Reaction equation

[F:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[F:1][C:2]1[C:9]([O:10][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

Procedure

2-Fluoro-3-hydroxybenzaldehyde (16.49 g) was dissolved in dimethylformamide (200 ml) and stirred under an argon atmosphere. Sodium hydride was added (60% in mineral oil, 5.18 g) and the mixture was stirred for 30 minutes. Benzyl bromide was added (16.8 ml) and the mixture was stirred overnight. Reaction mixture was concentrated in vacuo and the resulting residue was partitioned between diethyl ether (200 ml) and water (200 ml). Combined organic extracts were washed with water (400 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography, using a gradient of 0-10% ethyl acetate/iso-hexane as eluent to give the product as a yellow solid (18.41 g) 1H NMR (DMSO-d6) δ 5.20(s, 2H), 7.2-7.6(m, 8H), 10.21(s, 1H)