Dimethyl Sulfide → (4-Bromo-2-methylphenyl)methanol

HRID 2194864Notes

Reaction equation

HRID 2194864 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.S(C)C>C1COCC1>[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 1068Dimethyl SulfideHCID 995704-Bromo-2-methylbenzoic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 22280088(4-Bromo-2-methylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Borane-dimethyl sulfide complexe (2.5 eq.) was added to a stirred solution of commercially available 4-bromo-2-methylbenzoic acid (1 eq.) in THF (0.3M). The mixture was reflux for 3 h. at without a condensor allowing the SMe2 to escape. The final reaction concentration was 0.5M. The mixture was cooled to 0° C. and quenched with a slow addition of HCl 1N. The resulting mixture was extracted with Et2O. The organic extract was washed with water, brine, dried over MgSO4 filtered and concentrated to afford the desired material as a yellow solid.

Workup

  1. temperatureThe mixture was reflux for 3 h. at without a condensor
  2. customThe final reaction concentration was 0.5M
  3. customquenched with a slow addition of HCl 1N
  4. extractionThe resulting mixture was extracted with Et2O
  5. extractionThe organic extract
  6. washwas washed with water, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-652236a2588f40f893d5aeb1d88f9481
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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