Boron tribromide → Phenol, cyclohexyl-3(or 4)-methyl-

HRID 2100655Notes

Reaction equation

HRID 2100655 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([O:13]C)=[CH:9][C:8]=2[CH3:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>C(Cl)Cl>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=2[CH3:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 685261781-Cyclohexyl-4-methoxy-2-methylbenzene

Product 1

HCID 3085662Phenol, cyclohexyl-3(or 4)-methyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of crude 1-cyclohexyl-4-methoxy-2-methyl-benzene in dry DCM (10 mL) is added BBr3 at −78° C. Following this addition, the mixture is heated at 50° C. for 12 hours. The reaction mixture is cooled in an ice bath, and the reaction is quenched by the dropwise addition of water. The mixture is extracted with DCM. The combined organic phases are washed with 10% NaHCO3 (aq), brine, and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (10% EtOAc in hexanes) to give 4-cyclohexyl-3-methyl-phenol.

Workup

  1. additionthis addition
  2. temperatureThe reaction mixture is cooled in an ice bath
  3. customthe reaction is quenched by the dropwise addition of water
  4. extractionThe mixture is extracted with DCM
  5. washThe combined organic phases are washed with 10% NaHCO3 (aq), brine
  6. dry with materialdried over Na2SO4
  7. concentrationAfter concentration
  8. customthe residue is purified by silica gel chromatography (10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8c31867f27124324a967d4f0af7bc9d4
Source dataset
uspto-grants-2009_08
Patent number
US07572811B2

Reaction notes

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