Sodium borohydride → HCID 58494037, compound

HRID 1942697Notes

Reaction equation

HRID 1942697 reaction equation
[Br:1][C:2]1[C:3]([CH2:10][CH3:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[BH4-].[Na+]>CO>[Br:1][C:2]1[C:3]([CH2:10][CH3:11])=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57506022HCID 57506022, compound

Product 1

HCID 58494037HCID 58494037, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-bromo-2-ethylbenzaldehyde (5 g, 23.47 mmol) in Methanol (50 mL) was added NaBH4 (1.776 g, 46.9 mmol) at 0° C. The reaction solution was stirred at room temperature for 2 hours. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate, washed with water, dried over sodium sulphate, concentrated and purified by ISCO column chromatography to afford (3-bromo-2-ethylphenyl)methanol (D133) (3 g) as an oil. MS (ES): C9H11BrO requires 213.99. found 197.0 (M+H+-18).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. custompurified by ISCO column chromatography

Sources & evidence

ORD record
ord-52b5562d3a404dc19a1d7688650a783c
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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