3-Bromo-5-methoxybenzoic acid → (3-Bromo-5-methoxyphenyl)methanol

HRID 1686432Notes

Reaction equation

HRID 1686432 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1)[C:11](O)=[O:12]>C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]([CH2:11][OH:12])[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1

Participants

4

Reactant 2

HCID 40600483-Bromo-5-methoxybenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 10608788(3-Bromo-5-methoxyphenyl)methanolYield 112.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1M in THF, 22.07 ml) was added dropwise to a stirred solution of the product of step (ii) (5.1 g) in THF (50 ml) at 0° C. and stirred at RT overnight. The reaction was quenched in 2M HCl, extracted with ether, dried (MgSO4) and evaporated under reduced pressure to give an oil, which was purified by flash column chromatography (eluent 1:1 isohexane/diethylether) to give the subtitle compound (5.38 g).

Workup

  1. customThe reaction was quenched in 2M HCl
  2. extractionextracted with ether
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto give an oil, which
  6. customwas purified by flash column chromatography (eluent 1:1 isohexane/diethylether)

Sources & evidence

ORD record
ord-8e9f2f33d11c4840a6f793cb7b9ca898
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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