3-Bromo-4-methoxybenzaldehyde → (3-Bromo-4-methoxyphenyl)methanol

HRID 1370116Notes

Reaction equation

HRID 1370116 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[BH4-].[Na+]>C(O)C.O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][OH:6]

Participants

5

Reactant 2

HCID 986623-Bromo-4-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 13551346(3-Bromo-4-methoxyphenyl)methanolYield 99.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-bromo-4-methoxybenzaldehyde (4.98 g) in ethanol (50 mL) and tetrahydrofuran (10 mL) was added sodium borohydride (1.31 g) under ice-water cooling. The mixture was stirred at 0° C. for 2 hours. After evaporation of the solvent, the residue was partitioned between ethyl acetate and water. The separated organic layer was washed successively with water and brine, and dried over magnesium sulfate. The organic layer was evaporated in vacuo to give 3-bromo-4-methoxybenzyl alcohol as a colorless oil (4.98 g).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe separated organic layer was washed successively with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe organic layer was evaporated in vacuo

Sources & evidence

ORD record
ord-7f78ab457c67489ab445aa5a1d7bd82d
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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