Benzyl Bromide Reductive Bromination of an Acetal

Benzyl Bromide [Reductive Bromination of an Acetal].506 To a suspension of tin(II) bromide (5.1 mg, 0.02 mmol) and benzaldehyde dimethyl acetal (54.8 mg, 0.36 mmol) in CH2C12 (2.5 mL) were added successively Et3SiH (65.0 mg, 0.56 mmol) and acetyl bromide (96.8 mg, 0.79 mmol) in CH2C12 (1 mL) at room temperature under an argon atmosphere. The mixture was stirred for 3 hours at room temperature and quenched with a phosphate buffer (pH 7). 

The organic materials were extracted with CH2CI2 and the extract was dried over Na2S( 4. Benzyl bromide (54.7 mg, 89%) was isolated by TLC on Si02. 

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