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

HRID 2100655ノート

反応式

HRID 2100655 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8c31867f27124324a967d4f0af7bc9d4
出典データセット
uspto-grants-2009_08
特許番号
US07572811B2

反応ノート

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