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

HRID 1396069ノート

反応式

HRID 1396069 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 80%

実験手順

3.0 g N-(2-Bromo-phenyl)-2,2,2-trifluoro-acetamide was added in three portions to 3.74 mL (5.0 equiv.) chlorosulfonic acid under cooling in an ice-bath. The ice-bath was removed, the mixture was warmed to room temperature, and subsequently stirred for 1 hour at 80° C. After cooling, the clear brown reaction mixture was poured into ice and extracted with DCM. The organic phase was dried over Na2SO4, filtered, and evaporated to dryness to give 3.36 g (80%) of an oil that solidified upon standing. 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. temperatureAfter cooling
  4. additionthe clear brown reaction mixture was poured into ice
  5. extractionextracted with DCM
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness

出典と根拠

ORDレコード
ord-459c7161304a4939be360e0f2a5f3661
出典データセット
uspto-grants-2014_12
特許番号
US08901108B2

反応ノート

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