3,5-Dibromobenzaldehyde → (3,5-Dibromophenyl)methanol

HRID 1657166Notes

Reaction equation

HRID 1657166 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([Br:12])[CH:11]=1)[CH:7]=[O:8]>CO.C(OCC)(=O)C.C(Cl)Cl>[Br:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([Br:12])[CH:11]=1)[CH2:7][OH:8]

Participants

6

Reactant 2

HCID 6220773,5-DibromobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 7009423(3,5-Dibromophenyl)methanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.14G(30 mM) of sodium borohydride was added slowly to a suspension of 3,5-dibromobenzaldehyde (7.92G; 30 mM), from step (a), in 50 mL of methanol at 0° under nitrogen. After stirring 30 mins., the reaction mixture was diluted with 150 mL of ethyl acetate and washed with 5×50 mL of saturated sodium chloride solution, dried over anhydrous magnesium sulfate. Solvent removal afforded a crude product, which was dissolved in minimum amount of CH2Cl2 and applied on silica gel. Elution with 1:2 mixture of EtOAc:hexane gave 7.2G of the desired alcohol as white solid.

Workup

  1. washwashed with 5×50 mL of saturated sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customSolvent removal
  4. customafforded a crude product, which
  5. washElution
  6. additionwith 1:2 mixture of EtOAc

Sources & evidence

ORD record
ord-1bccf3eb2bd541c6aa1451531fc02844
Source dataset
uspto-grants-1993_10
Patent number
US05256777

Reaction notes

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