5-Bromo-2-methoxybenzaldehyde → 5-Bromo-2-methoxybenzyl alcohol

HRID 1158466Notes

Reaction equation

HRID 1158466 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH2:7][OH:8])[CH:9]=1

Participants

4

Reactant 2

HCID 906845-Bromo-2-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 6122985-Bromo-2-methoxybenzyl alcohol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

To a suspension of 5-bromo-2-methoxy-benzaldehyde (7.00 g, 32.2 mmol) in MeOH (40 mL), cooled to 0 to 5° C., is added NaBH4 (1.40 g, 35.4 mmol). After stirring for 1 h, the mixture is poured into ice-water, followed by extraction with AcOEt. The combined organics are washed with brine, dried (Na2SO4) and concentrated to give the title product as off-white solid. TLC, Rf (hexane/AcOEt 3:1)=0.19. 1H-NMR (CDCl3): δ 2.24 (m, 2H), 3.88 (s, 3H), 4.68 (d, 2H), 6.79 (dd, 1H), 7.41 (dd, 1H), 7.45 (d, 1H) ppm.

Workup

  1. extractionfollowed by extraction with AcOEt
  2. washThe combined organics are washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-071f0d3d70da4e82a2a27309cf0553e0
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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