2-Bromo-5-hydroxybenzaldehyde → 4-bromo-3-(hydroxymethyl)phenol

HRID 1483636Notes

Reaction equation

HRID 1483636 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH:9]=[O:10].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 3871792-Bromo-5-hydroxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 207854984-bromo-3-(hydroxymethyl)phenolYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromo-3-formylphenol (20.1 g, 100 mmol) in methanol (200 mL) was added sodium borohydride (1.90 g, 50.0 mmol) portionwise at 0° C., and the mixture was stirred at room temperature for 1 h. The solvent was removed under reduced pressure to a half volume, 6 M HCl (50 mL) was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 4-bromo-3-hydroxymethylphenol (19.4 g, 96%).

Workup

  1. customThe solvent was removed under reduced pressure to a half volume, 6 M HCl (50 mL)
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ab865f7833b24359a958400f7c3e58d5
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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