Benzoyl Peroxide → 2-(Bromomethyl)-5-fluoro-1,3-benzothiazole

HRID 1597822

Reaction equation

HRID 1597822 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:19][C:20]1[S:21][C:22]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:23]=2[N:24]=1.[Br:30]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:30][CH2:19][C:20]1[S:21][C:22]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:23]=2[N:24]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5974375-Fluoro-2-methylbenzothiazole

Product 1

HCID 144586272-(Bromomethyl)-5-fluoro-1,3-benzothiazoleYield 7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

127 mg of dibenzoyl peroxide were added to a solution of 8.79 g of 2-methyl-5-fluorobenzothiazole and 20.6 g of N-bromosuccinimide in 88 ml of carbon tetrachloride at room temperature and the resulting mixture was stirred under reflux for 6 hours. At the end of this time, the reaction mixture was filtered and the resulting filtrate was concentrated by evaporation under reduced pressure to give a crude crystalline solid which was purified by column chromatography through silica gel using a 10:1 by volume mixture of hexane and ethyl acetate to give 850 mg (yield 7%) of the title compound as a solid.

Workup

  1. temperatureunder reflux for 6 hours
  2. filtrationAt the end of this time, the reaction mixture was filtered
  3. concentrationthe resulting filtrate was concentrated by evaporation under reduced pressure
  4. customto give a crude crystalline solid which
  5. customwas purified by column chromatography through silica gel using a 10:1
  6. additionby volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-6dd87ec0a4814c59ad7acd04363dc907
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Linked notes

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