Benzoyl Peroxide → 2-(Bromomethyl)-7-chloro-1,3-benzothiazole

HRID 1157399Notes

Reaction equation

HRID 1157399 reaction equation
[Cl:1][C:2]1[C:10]2[S:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:8]1[S:9][C:10]2[C:2]([Cl:1])=[CH:3][CH:4]=[CH:5][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 10583610HCID 10583610, compound

Product 1

HCID 218828992-(Bromomethyl)-7-chloro-1,3-benzothiazoleYield 6.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 900 mg (4.9 mmol) of 7-chloro-2-methyl-1,3-benzothiazole (16-4), 1.13 g (6.37 mmol) of N-bromosuccinimide and 47 mg (0.196 mmol) of benzoyl peroxide in CCl4 (25mL) was refluxed under irradiation by a UV lamp for 4 hours. After this time the reaction was cooled to room temperature and the insolubles were filtered off. The reaction was purified on a silica column eluted with EtOAc:hexanes (3:97 to 1:1) and 80 mg of the desired product 16-5 was isolated. HRMS: measured 261.9080; theoretical 261.9087. 1H NMR (CDCl3): 4.80 (s, 2H), 7.43 (m, 2H), 7.92 (d, 1H).

Workup

  1. temperaturewas refluxed under irradiation by a UV lamp for 4 hours
  2. filtrationthe insolubles were filtered off
  3. customThe reaction was purified on a silica column
  4. washeluted with EtOAc:hexanes (3:97 to 1:1)

Sources & evidence

ORD record
ord-e6a34a0b0a5f4530b72c5929d01d7b06
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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