N,N-Dimethylaniline → Methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-hydroxybenzoate

HRID 2177727노트

반응식

HRID 2177727 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[C:7]([O:27]C)=[C:8]([C:13]([CH2:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)(=[O:19])=[O:18])=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10].CN(C)C1C=CC=CC=1>C(Cl)Cl>[Br:5][C:6]1[C:7]([OH:27])=[C:8]([C:13]([CH2:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)(=[O:19])=[O:18])=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10]

참가 물질

5

반응물 3

HCID 949N,N-DimethylanilineHCID 6451240Aluminum(III) ChlorideHCID 67107903Methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-methoxybenzoate2회

생성물 1

HCID 67107545Methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-hydroxybenzoate수율 82.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Aluminium chloride (0.7 g) was added to a stirred solution of methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-methoxybenzoate (Intermediate 68, 0.76 g) and N,N-dimethylaniline (1.27 g) in DCM (8 ml) and the resultant mixture was stirred for 30 minutes. The mixture was partitioned between ethyl acetate and hydrochloric acid (1M) and the organic layer was washed with sodium bicarbonate (saturated aqueous solution), dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with ether. The solid was collected by filtration to give methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-hydroxybenzoate (0.61 g) as a white solid.

후처리

  1. customThe mixture was partitioned between ethyl acetate and hydrochloric acid (1M)
  2. washthe organic layer was washed with sodium bicarbonate (saturated aqueous solution)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was triturated with ether
  7. filtrationThe solid was collected by filtration

출처 및 근거

ORD 기록
ord-1d9cded88b564d32aaa1bfe7c869971c
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067905B2

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