3-Bromobenzaldehyde → 3-Bromobenzyl alcohol

HRID 564469Notes

Reaction equation

HRID 564469 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[BH4-].[Na+]>CCO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][CH:9]=1

Participants

4

Procedure

To a solution of 3-bromobenzaldehyde (114.8 g, 620.4 mmol) in EtOH (650 mL), NaBH4 (7.1 g, 186.1 mmol) was added in several portions 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 filter 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 filter 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-fd6be139b26d4c7a842b1521f0a2edb7
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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