3,5-Dibromosalicylaldehyde → 2,4-dibromo-6-(hydroxymethyl)phenol

HRID 1400788Notes

Reaction equation

HRID 1400788 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:4]([CH:5]=[O:6])[C:3]=1[OH:11].[BH4-].[Na+]>CO>[OH:11][C:3]1[C:2]([Br:1])=[CH:9][C:8]([Br:10])=[CH:7][C:4]=1[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 70243,5-DibromosalicylaldehydeHCID 4311764Sodium borohydride2×

Product 1

HCID 6375582,4-dibromo-6-(hydroxymethyl)phenolYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3,5-dibromosalicylaldehyde (10.6 grams, 38 mmol) in MeOH (70 mL), was added NaBH4 (4.3 grams, 115 mmol) in small portions and the solution was stirred for 1.5 hours. Another batch of NaBH4 (2.0 grams, 52 mmol) was added in small portions and the mixture was stirred for another 2 hours. The solvent was removed under vacuum and the resulting white solid was re-precipitated in water. The product was collected as a white solid by vacuum filtration (10.1 grams, 94% yield).

Workup

  1. stirringthe mixture was stirred for another 2 hours
  2. customThe solvent was removed under vacuum
  3. customthe resulting white solid was re-precipitated in water
  4. filtrationThe product was collected as a white solid by vacuum filtration (10.1 grams, 94% yield)

Sources & evidence

ORD record
ord-3c3d40d618f845729cf09fb9e3238eef
Source dataset
uspto-grants-2014_12
Patent number
US08907032B2

Reaction notes

Loading…