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

HRID 1484441Notes

Reaction equation

HRID 1484441 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 85%

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9161a221de6246a5a4d4b228c1cf8963
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

Loading…