Sodium borohydride → 4,4'-Dibromo-2,2'-bis-hydroxymethyl-biphenyl

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Reaction Conditions

Reaction Steps

The solution of 2,7-dibromo-phenanthrene (3.8 g) in DCM/MeOH (120 ml/1 ml) was cooled to −78° C., and it became a suspension. Ozone was bubbled thorough for 20 minutes, and the mixture became blue. Oxygen was bubbled for 5 minutes and dimethyl sulfide (3 ml) was added. The mixture was warmed to 25° C. and stirred for 12 hours. Concentration and purification by flash column chromatography (hexanes/EtOAc) gave 4,4′-dibromo-biphenyl-2,2′-dicarbaldehyde (600 mg). To the solution of 4,4′-dibromo-biphenyl-2,2′-dicarbaldehyde (600 mg, 1.7 mmol) in THF/MeOH (10 ml/10 ml) at 0° C. was added sodium borohydride (320 mg, 8.2 mmol). The mixture was warmed to 25° C. and stirred for 12 hours. The mixture was quenched with water, and extracted with EtOAc. The organic phase was washed with water and brine, and was dried with sodium sulfate. Concentration gave (4,4′-dibromo-2′-hydroxymethyl-biphenyl-2-yl)-methanol (550 mg).

Provenance & Evidence