Ammonium Chloride → (4-Bromo-3-methylphenyl)methanol

HRID 250858Notes

Reaction equation

HRID 250858 reaction equation
[BH4-].[Li+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[Br:14])[C:7](OC)=[O:8].[Cl-].[NH4+]>O1CCCC1>[Br:14][C:13]1[CH:12]=[CH:11][C:6]([CH2:7][OH:8])=[CH:5][C:4]=1[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 3294148Methyl 4-bromo-3-methylbenzoateHCID 4148881Lithium borohydride

Product 1

HCID 10987288(4-Bromo-3-methylphenyl)methanolYield 104.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

284 mg (12.9 mmol, 3 eq) of lithium borohydride are added to a solution of 1.0 g (4.3 mmol, 1 eq) of methyl 3-methyl-4-bromobenzoate in 10 ml of tetrahydrofuran. The reaction mixture is stirred at 60° C. for 12 hours. The reaction medium is hydrolyzed with ammonium chloride solution and extracted with ethyl acetate. The organic phases are combined, washed with sodium chloride solution and dried over sodium sulfate. 900 mg of (4-bromo-3-methylphenyl)methanol are obtained in oil form and used in the following reaction without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with sodium chloride solution
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-248d93701dd240b08ba4e4ee8037fabb
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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