Benzoyl Peroxide → 4-(Bromomethyl)-3,5-difluorobenzenesulfonamide

HRID 83897Notes

Reaction equation

HRID 83897 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:5]=[C:6]([F:9])[C:7]=1[CH3:8].[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:5][C:6]=1[F:9]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 66740770HCID 66740770, compound

Product 1

HCID 667398554-(Bromomethyl)-3,5-difluorobenzenesulfonamideYield 30.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3,5-difluoro-4-methylbenzenesulfonamide (1.237 g, 6 mmol), N-bromosuccinimide (1.4 g, 1.3 eq) and benzoyl peroxide (87 mg, 0.1 eq) in carbon tetrachloride (24 mL) was heated to reflux for 6 h under a halogen light. After the reaction was determined to be complete by GC-MS, the mixture was concentrated and purified by column chromatography (silica, EtOAc-hexane, 1:4 to 4:1) to give the title compound (524 mg). 1H NMR (400 MHz, CD3OD) δ 7.75 (d, 2H), 4.83 (s, 3H); GC-MS (ES) m/z 285 (M+), 287 (M+2).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 h under a halogen light
  3. concentrationthe mixture was concentrated
  4. custompurified by column chromatography (silica, EtOAc-hexane, 1:4 to 4:1)

Sources & evidence

ORD record
ord-ff2495fe8c604da880a3932136d32811
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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