Water → 1-Methoxy-2-(methylsulfonyl)benzene

HRID 1093752ノート

反応式

HRID 1093752 の反応式
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20][CH3:21].[OH2:22]>C(Cl)Cl>[CH3:21][S:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[O:13][CH3:12])(=[O:9])=[O:22]

参加物

5

反応物 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 137577Benzene, 1-methoxy-2-(methylthio)-

生成物 1

HCID 27596911-Methoxy-2-(methylsulfonyl)benzene収率 91.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

m-Chloroperbenzoic acid (280 mg, 1.62 mmol) was added to a cold (0-4° C.) solution of 1-methoxy-2-methylsulfanyl-benzene (100 mg, 0.64 mmol) in DCM (3 mL) and stirring was continued for 1 hr. The reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was washed with saturated brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford 110 mg (91.6% Yield) of 1-methanesulfonyl-2-methoxy-benzene. Boron tribromide (370 mg, 1.47 mmol) was added to a cold solution (−70° C.) solution of 1-methanesulfonyl-2-methoxy-benzene (10 mg, 0.591 mmol) in DCM (2 mL) and stirring was continued for 10 minutes. After which the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was washed with saturated brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford 65 mg (64.35% Yield) of 2-methanesulfonyl-phenol. 2-Methylsulfonyl-phenol was converted to 4-(2-methanesulfonyl-phenoxy)-piperidine hydrochloride according to Step 1 of the General Scheme).

後処理

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with saturated brine solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-556ce52217284d9695625a422f651345
出典データセット
uspto-grants-2012_03
特許番号
US08129376B2

反応ノート

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