4-Bromo-2-methylbenzoic acid → (4-Bromo-2-methylphenyl)methanol

HRID 2366511Notes

Reaction equation

HRID 2366511 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>O1CCCC1>[Br:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][OH:11])=[C:8]([CH3:15])[CH:7]=1

Participants

4

Reactant 2

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

Product 1

HCID 22280088(4-Bromo-2-methylphenyl)methanolYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-dimethyl sulfide complex (2M in THF; 116 mL, 0.232 mol) is added slowly to a solution of 4-bromo-2-methylbenzoic acid (24.3 g, 0.113 mol) in anhydrous tetrahydrofuran (THF, 146 mL) at 3° C. After stirring cold for 10 min the cooling bath is removed and the reaction is allowed to warm slowly to ambient temperature. After 1 hour, the solution is cooled to 5° C., and water (100 mL) is added slowly. Ethyl acetate (100 mL) is added and the phases are separated. The organic layer is washed with saturated aqueous NaHCO3 solution (200 mL) and dried over Na2SO4. Filtration and concentration under reduced pressure gives a residue which is purified by filtration through a short pad of silica eluting with 15% ethyl acetate/iso-hexane to give the title compound (20.7 g, 91.2% yield). MS (m/z): 183/185 (M+1-18).

Workup

  1. customis removed
  2. waitAfter 1 hour
  3. temperaturethe solution is cooled to 5° C.
  4. additionwater (100 mL) is added slowly
  5. additionEthyl acetate (100 mL) is added
  6. customthe phases are separated
  7. washThe organic layer is washed with saturated aqueous NaHCO3 solution (200 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationFiltration and concentration under reduced pressure
  10. customgives a residue which
  11. filtrationis purified by filtration through a short pad of silica eluting with 15% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-98280d4a117943ffad38502c34a01bd6
Source dataset
uspto-grants-2014_04
Patent number
US08697849B2

Reaction notes

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