Benzoyl Peroxide → 5-Bromo-2-(bromomethyl)-1,3-benzothiazole

HRID 2165064Notes

Reaction equation

HRID 2165064 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:5]=2[N:6]=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][CH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 30174575-Bromo-2-methylbenzothiazole

Product 1

HCID 144586425-Bromo-2-(bromomethyl)-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-methyl-5-bromobenzothiazole (32.0 g), N-bromosuccinimide (25.1 g), carbon tetrachloride (700 ml) and a catalytic amount of benzoyl peroxide (0.2 g) was refluxed under irradiation by an UV lamp for 14 hours. The reaction mixture was cooled to room temperature, filtered to remove the precipitated succinimide and the filtrate was evaporated to dryness. The resulting solid was chromatographed over silica gel to obtain the product (7.8 g; m.p. 107° C.).

Workup

  1. filtrationfiltered
  2. customto remove the precipitated succinimide
  3. customthe filtrate was evaporated to dryness
  4. customThe resulting solid was chromatographed over silica gel
  5. customto obtain the product (7.8 g; m.p. 107° C.)

Sources & evidence

ORD record
ord-68dea79663254e25a8d94dd5074b23f0
Source dataset
uspto-grants-1990_07
Patent number
US04939140

Reaction notes

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