2-Chloro-5-(2-oxo-propyl)-benzenesulfonamide → 5-(1-Bromo-2-oxo-propyl)-2-chloro-benzenesulfonamide

HRID 908170Notes

Reaction equation

HRID 908170 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[S:12]([NH2:15])(=[O:14])=[O:13].C1C=C[NH+]=CC=1.[Br:22][Br-]Br>C1COCC1>[Br:22][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([S:12]([NH2:15])(=[O:14])=[O:13])[CH:4]=1)[C:9](=[O:11])[CH3:10]

Participants

3

Reactant 1

HCID 673923132-Chloro-5-(2-oxo-propyl)-benzenesulfonamide

Product 1

HCID 866062175-(1-Bromo-2-oxo-propyl)-2-chloro-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2-chloro-5-(2-oxo-propyl)-benzenesulfonamide (33a) (1.4 g, 5.7 mmol) in dry THF (100 ml) at room temperature is treated with polymer supported pyridine hydrobromide perbromide (2.9 g, 5.7 mmol) and left to stir overnight. The reaction mixture is then filtered and the solvent removed in vacuo. The residue is purified by chromatography on silica eluting with 1:4 ethyl acetate-hexane to give the titled compound.

Workup

  1. waitleft
  2. filtrationThe reaction mixture is then filtered
  3. customthe solvent removed in vacuo
  4. customThe residue is purified by chromatography on silica eluting with 1:4 ethyl acetate-hexane

Sources & evidence

ORD record
ord-fa16fbc243584ccc954fa7c37f7cfb21
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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