Water → (4-Bromo-2-methylphenyl)methanol

HRID 1625930Notes

Reaction equation

HRID 1625930 reaction equation
CSC.B.[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[C:8]([CH3:15])[CH:7]=1.O>O1CCCC1>[Br:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][OH:11])=[C:8]([CH3:15])[CH:7]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 995704-Bromo-2-methylbenzoic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 22280088(4-Bromo-2-methylphenyl)methanolYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-dimethyl sulfide complex (2M in THF; 1150 mL, 2.3 mol) is added over 1.5 hours to a solution of 4-bromo-2-methylbenzoic acid (250 g, 1.16 mol) in anhydrous tetrahydrofuran (1500 mL) at 0° C. The reaction is allowed to warm slowly to ambient temperature and stirred overnight. The solution is cooled to −10° C. and water (500 mL) is added very slowly. Further water (5000 mL) is added and the mixture is extracted with ethyl acetate (2×5000 mL). The combined organic layers are washed with saturated aqueous NaCl solution (5000 mL) and dried over Na2SO4. Filtration and concentration under reduced pressure provides the title compound (226 g, 97% yield).

Workup

  1. temperatureThe solution is cooled to −10° C.
  2. extractionthe mixture is extracted with ethyl acetate (2×5000 mL)
  3. washThe combined organic layers are washed with saturated aqueous NaCl solution (5000 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-697a3128a76048bcbc6a98b9d52e27f7
Source dataset
uspto-grants-2014_07
Patent number
US08785404B2

Reaction notes

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