N-bromobutanimide → 3-(Bromomethyl)-2,4-dichlorobenzene-1-sulfonyl chloride

HRID 321955Notes

Reaction equation

HRID 321955 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:15]([CH3:16])=[C:14]([Cl:17])[CH:13]=[CH:12][C:11]=1[S:18]([Cl:21])(=[O:20])=[O:19]>ClC(Cl)C(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][CH2:16][C:15]1[C:10]([Cl:9])=[C:11]([S:18]([Cl:21])(=[O:20])=[O:19])[CH:12]=[CH:13][C:14]=1[Cl:17]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 157253742,4-Dichloro-3-methylbenzene-1-sulfonyl chloride

Product 1

HCID 158190763-(Bromomethyl)-2,4-dichlorobenzene-1-sulfonyl chlorideYield 47.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 65911,1,2,2-TetrachloroethaneSolvent

Conditions

Temperature
120 °C

Procedure

85.44 g (0.48 mol) of N-bromosuccinimide and then 200 mg of benzoyl peroxide are added to a solution, at room temperature, of 41.52 g (0.16 mol) of 2,4-dichloro-3-methylbenzenesulfonyl chloride in 150 ml of 1,1,2,2-tetrachloroethane. The reaction mixture is heated at 120° C. for 2 hours. It is cooled and filtered and the filtrate is washed successively with water, with saturated sodium bicarbonate solution and finally with water until the washings are neutral. The organic phase collected from the filtrate is then dried over magnesium sulfate and concentrated. Recrystallization from hexane gives 25.53 g of the expected product in the form of white crystals (yield =47%).

Workup

  1. temperatureIt is cooled
  2. filtrationfiltered
  3. washthe filtrate is washed successively with water, with saturated sodium bicarbonate solution and finally with water until the washings
  4. customThe organic phase collected from the filtrate
  5. dry with materialis then dried over magnesium sulfate
  6. concentrationconcentrated
  7. customRecrystallization from hexane

Sources & evidence

ORD record
ord-cb06987a3a8e4b059a36e8dd01ffa744
Source dataset
uspto-grants-2001_04
Patent number
US06211181B1

Reaction notes

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