3-Bromobenzaldehyde → 3-Bromobenzyl alcohol

HRID 662049Notes

Reaction equation

HRID 662049 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8]>CCO>[Br:3][C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:9]=[CH:10][CH:11]=1

Participants

4

Procedure

Sodium borohydride (7.1 g, 186.1 mmol) in several portions was added to a solution of 3-bromobenzaldehyde (114.8 g, 620.4 mmol) in EtOH (650 mL) at 25° C. Then the mixture was stirred for 1 h at room temperature. The reaction was quenched with water (200 mL). After removing EtOH, the residue was dissolved in AcOEt (500 mL), and filtered. The filtrate was washed with water (150 mL), brine (150 mL), and dried over Na2SO4. After removing the solvent, 115.8 g of the title compound was obtained (yield: 99.8%).

Workup

  1. customThe reaction was quenched with water (200 mL)
  2. customAfter removing EtOH
  3. dissolutionthe residue was dissolved in AcOEt (500 mL)
  4. filtrationfiltered
  5. washThe filtrate was washed with water (150 mL), brine (150 mL)
  6. dry with materialdried over Na2SO4
  7. customAfter removing the solvent

Sources & evidence

ORD record
ord-5f19d28549e247bb8a6a9aa376f7c79a
Source dataset
uspto-grants-2011_12
Patent number
US08084449B2

Reaction notes

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