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

HRID 1664323Notes

Reaction equation

HRID 1664323 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-e8f99372d7844742b498d4ca73613f83
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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