Bromine → 5-(2-Bromoacetyl)-2-fluorobenzenesulphonamide

HRID 1390913Notes

Reaction equation

HRID 1390913 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([F:14])=[C:8]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:9]=1)(=[O:3])[CH3:2].[Br:15]Br>C(O)(=O)C.Br>[Br:15][CH2:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([F:14])=[C:8]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:9]=1)=[O:3]

Participants

5

Reactant 2

HCID 24408BromineHCID 213316525-Acetyl-2-fluorobenzenesulphonamide

Product 1

HCID 118085905-(2-Bromoacetyl)-2-fluorobenzenesulphonamide

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 176Acetic AcidSolvent3×

Procedure

A solution of 5-acetyl-2-fluorobenzenesulphonamide (1.0 g) in acetic acid (30 ml) was treated dropwise with a solution of bromine (0.736 g) in acetic acid (4.5 ml) at 50° in the presence of a few drops of 48% hydrogen bromide in acetic acid. After stirring for 15-20 minutes, the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (50 ml) and washed with 8% sodium bicarbonate (50 ml) and water (50 ml). The organic layer was then dried (MgSO4) and concentrated to give a pale brown oil which crystallised from benzene/acetone, 1.2 g, m.p. 129-132°.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  3. washwashed with 8% sodium bicarbonate (50 ml) and water (50 ml)
  4. dry with materialThe organic layer was then dried (MgSO4)
  5. concentrationconcentrated
  6. customto give a pale brown oil which
  7. customcrystallised from benzene/acetone, 1.2 g, m.p. 129-132°

Sources & evidence

ORD record
ord-0cc63bf2d59c4a8ba190af396f847a28
Source dataset
uspto-grants-1979_02
Patent number
US04140713

Reaction notes

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