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

HRID 1396069노트

반응식

HRID 1396069 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

HCID 581587063-Bromo-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride수율 80%

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-459c7161304a4939be360e0f2a5f3661
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901108B2

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