Bromine → 4-Bromoacetyl-2-(fluoro)benzenesulfonamide

HRID 497262Notes

Reaction equation

HRID 497262 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[C:6]([F:14])[CH:5]=1)(=[O:3])[CH3:2].[Br:15]Br>C(O)(=O)C>[Br:15][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[C:6]([F:14])[CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 223169644-Acetyl-2-fluorobenzene-1-sulfonamide

Product 1

HCID 223166704-Bromoacetyl-2-(fluoro)benzenesulfonamideYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
70 °C

Procedure

To a suspension of 4-acetyl-2-(fluoro)benzenesulfonamide from step 1 (4.0 g, 18 mmol) in acetic acid (90 mL) was added dropwise a solution of bromine (2.9 g, 18 mmol) in acetic acid (10 mL) at 40° C. The mixture was heated at 70° C. for 4 h. After cooled to room temperature, the mixture was concentrated and the residual brown solid was recrystallized from ethyl acetate-hexane to give the title compound (3.2 g, 60%).

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthe mixture was concentrated
  3. customthe residual brown solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7c63c261b905493eb31978acc3540086
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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