2-Bromo-5-fluorobenzaldehyde → 2-Bromo-5-fluorobenzyl alcohol

HRID 1013149Notes

Reaction equation

HRID 1013149 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 27733212-Bromo-5-fluorobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 27733492-Bromo-5-fluorobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-bromo-5-fluoro-benzaldehyde (21.34 g, 105 mmole) in methanol (170 mL) was added at 0-5° C. portionwise NaBH4 (3.99 g, 105 mmole). At the end of the addition, the cooling bath was removed and the reaction mixture was stirred at room temperature for 2 h. On concentration, the solution generated a white solid that was added with water, filtered and dried under vacuum to yield compound PRE7 (19.23 g; white powder) (Yield=91 Rt: 10.64 min.

Workup

  1. additionAt the end of the addition
  2. customthe cooling bath was removed
  3. concentrationOn concentration
  4. additionthat was added with water
  5. filtrationfiltered
  6. customdried under vacuum
  7. customto yield compound PRE7 (19.23 g; white powder) (
  8. customYield=91 Rt: 10.64 min.

Sources & evidence

ORD record
ord-cfb7b46ac9f64cd18e6791a2d020c4fb
Source dataset
uspto-grants-2011_07
Patent number
US07981907B2

Reaction notes

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