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

HRID 1185631Notes

Reaction equation

HRID 1185631 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[O:18])[C:5]([C:8]2[C:9]([CH:15]=[O:16])=[CH:10][C:11]([Br:14])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1.[BH4-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[CH2:15][OH:16])=[C:4]([CH2:17][OH:18])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 113260944,4'-Dibromobiphenyl-2,2'-dicarbaldehyde

Product 1

HCID 113721754,4'-Dibromo-2,2'-bis-hydroxymethyl-biphenylYield 87%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

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).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water and brine
  4. dry with materialwas dried with sodium sulfate
  5. concentrationConcentration

Sources & evidence

ORD record
ord-5b7f894d816f4ca1828684d5e0ea460d
Source dataset
uspto-grants-2014_03
Patent number
US08669234B2

Reaction notes

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