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

HRID 1256090Notes

Reaction equation

HRID 1256090 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:6][CH:7]=1.[Cl:15][S:16](O)(=[O:18])=[O:17]>>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:14])[C:10]([F:11])([F:13])[F:12])[CH:5]=[CH:6][C:7]=1[S:16]([Cl:15])(=[O:18])=[O:17]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 3574082N-(3-bromophenyl)-2,2,2-trifluoroacetamide

Product 1

HCID 609998842-Bromo-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride

Procedure

The crude N-(3-bromophenyl)-2,2,2-trifluoroacetamide was cooled to 0° C., then chlorosulfonic acid was added dropwise at 0° C. over 10 min. The r×n mix was stirred at 0° C. to rt overnight. LC/MS monitored the r×n. The r×n mix poured into ice-H2O (100 g) to quench the r×n. The sticky gum was washed with H2O and dried in vacuum to give the crude 2-bromo-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride.

Workup

  1. additionThe r×n mix
  2. additionThe r×n mix
  3. customto quench the r×n
  4. washThe sticky gum was washed with H2O
  5. customdried in vacuum

Sources & evidence

ORD record
ord-9701573f159541adbdcde76b4830161a
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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