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

HRID 1093752노트

반응식

HRID 1093752 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 27596911-Methoxy-2-(methylsulfonyl)benzene수율 91.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-556ce52217284d9695625a422f651345
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129376B2

반응 노트

불러오는 중…