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Dichloromethane → 5-Chloro-2-fluoro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide

HRID 706781
ノート
印刷プレビュー

反応式

HRID 706781 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.[CH3:13][C:14]1([CH3:28])[C:18]([CH3:20])([CH3:19])[O:17][B:16]([C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)[O:15]1.C(Cl)Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([S:8]([NH:27][C:24]2[CH:23]=[CH:22][C:21]([B:16]3[O:17][C:18]([CH3:20])([CH3:19])[C:14]([CH3:28])([CH3:13])[O:15]3)=[CH:26][CH:25]=2)(=[O:10])=[O:9])[CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 27782735-Chloro-2-fluorobenzenesulfonyl chloride

生成物 1

HCID 894637655-Chloro-2-fluoro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

5-Chloro-2-fluoro-benzenesulfonyl chloride (10.5 g) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (10.0 g) were added to a reaction vessel containing a magnetic stirring bar, followed by 200 ml dry DCM and 4.1 ml pyridine. The reaction mixture was stirred at RT for 20 h before being cooled on an ice-bath and quenched with 1M aqueous sodium hydroxide solution. The organic phase was separated and the aqueous phase acidified with 2M aqueous hydrochloric acid and extracted three times with EtOAc. The combined organic phases were washed with brine and dried over sodium sulfate and evaporated to afford the crude product. Purification by flash chromatography on silica gel using a mixture of EtOAc and heptane as the eluent afforded the title compound as a colorless solid after evaporation of the solvents under reduced pressure. Yield: 14.14 g (75%).

後処理

  1. additioncontaining a magnetic stirring bar
  2. temperaturebefore being cooled on an ice-bath
  3. customquenched with 1M aqueous sodium hydroxide solution
  4. customThe organic phase was separated
  5. extractionextracted three times with EtOAc
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto afford the crude product
  10. customPurification by flash chromatography on silica gel using
  11. additiona mixture of EtOAc and heptane as the eluent

出典と根拠

ORDレコード
ord-f021e77b60314d968ac32fde714d5243
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09174993B2

反応ノート

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