3-Bromo-4-fluorobenzaldehyde → 3-Bromo-4-fluorobenzyl Alcohol

HRID 2377297Notes

Reaction equation

HRID 2377297 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[O:6].[BH4-].[Na+]>CO.O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

5

Reactant 2

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 27733513-Bromo-4-fluorobenzyl Alcohol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-4-fluorobenzaldehyde (35.0 g, 172.4 mmol) in methanol (400 mL) and tetrahydrofuran (200 mL) was added sodium borohydride (6.5 g, 172.4 mmol) in portions at about 0° C. The mixture was stirred for about 3 h while being allowed to warm to ambient temperature. The solvents were removed under vacuum, the residue was diluted with water (600 mL) and was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and evaporated under reduced pressure to provide the desired product. MS (DCI-NH3): m/z 204, 206 (M)+.

Workup

  1. customThe solvents were removed under vacuum
  2. additionthe residue was diluted with water (600 mL)
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a3ee646b0e3a463b9adb25358b051328
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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