Chlorosulfonic acid → 3-Bromo-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride

HRID 1484441ノート

反応式

HRID 1484441 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11].[Cl:15][S:16](O)(=[O:18])=[O:17]>>[Br:1][C:2]1[CH:7]=[C:6]([S:16]([Cl:15])(=[O:18])=[O:17])[CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[C:10]([F:13])([F:11])[F:12]

参加物

3

反応物 2

HCID 24638Chlorosulfonic acidHCID 4263215N-(2-Bromophenyl)-2,2,2-trifluoroacetamide

生成物 1

HCID 581587063-Bromo-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride収率 85%

反応条件

温度
80 °C

実験手順

15.0 g (1.0 equiv). N-(2-Bromo-phenyl)-2,2,2-trifluoro-acetamide was added in four portions to 18.7 mL (5 mol equiv.) chlorosulfonic acid under cooling in an ice-bath. The ice-bath was removed, the mixture was warmed to room temperature and subsequently to 80° C. After stirring for 1 hour the mixture was cooled to room temperature and poured into ice. It was extracted with dichloromethane, dried over Na2SO4, filtered and evaporated to dryness to give 17.4 g (85%) 3-bromo-4-(2,2,2-trifluoro-acetylamino)-benzenesulfonyl chloride. 1H NMR (400 MHz, CDCl3) δ 8.09 (dd, J=9.0, 2.0 Hz, 1H), 8.30 (d, J=2.0 Hz, 1H), 8.69 (d, J=9.0 Hz, 1H), 8.71 (br.s., 1H).

後処理

  1. temperatureunder cooling in an ice-bath
  2. customThe ice-bath was removed
  3. temperaturewas cooled to room temperature
  4. additionpoured into ice
  5. extractionIt was extracted with dichloromethane
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness

出典と根拠

ORDレコード
ord-9161a221de6246a5a4d4b228c1cf8963
出典データセット
uspto-grants-2016_08
特許番号
US09422244B2

反応ノート

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