N-bromobutanimide → 1-(Bromomethyl)-4-(phenylsulfonyl)benzene

HRID 1903714Notes

Reaction equation

HRID 1903714 reaction equation
C1(C)C=CC=C[C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13]([C:16]2[CH:21]=[CH:20][C:19](C3C=CC=CC=3C)=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[Br:30]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:30][CH2:2][C:7]1[CH:12]=[CH:11][C:10]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 86739317p-Tolyl phenylsulphone

Product 1

HCID 2641001-(Bromomethyl)-4-(phenylsulfonyl)benzeneYield 171.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of p-tolyl phenylsulphone (20 g) in refluxing CCl4 (400 ml) containing dibenzoyl peroxide (0.4 g) was treated with N-bromosuccinimide (15.3 g) in portions rapidly. The mixture was heated under reflux for 30 min., filtered whilst hot and the filtrate allowed to cool. Evaporation gave the title compound (26.8 g), m.p. (103°-104°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 min.
  3. filtrationfiltered whilst hot and the filtrate
  4. temperatureto cool
  5. customEvaporation

Sources & evidence

ORD record
ord-95cb870c4edd41fd92c92ca6e0141477
Source dataset
uspto-grants-1984_03
Patent number
US04438112

Reaction notes

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