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

HRID 1396069Notes

Reaction equation

HRID 1396069 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-459c7161304a4939be360e0f2a5f3661
Source dataset
uspto-grants-2014_12
Patent number
US08901108B2

Reaction notes

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