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

HRID 2177727ノート

反応式

HRID 2177727 の反応式
[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]

参加物

5

反応物 3

HCID 949N,N-DimethylanilineHCID 6451240Aluminum(III) ChlorideHCID 67107903Methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-methoxybenzoate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1d9cded88b564d32aaa1bfe7c869971c
出典データセット
uspto-grants-2015_06
特許番号
US09067905B2

反応ノート

読み込み中…