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

HRID 2100655노트

반응식

HRID 2100655 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8c31867f27124324a967d4f0af7bc9d4
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572811B2

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