Benzoyl Peroxide → 2-(4-(Bromomethyl)phenyl)benzo[d]thiazole

HRID 224315Notes

Reaction equation

HRID 224315 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1.[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][Br:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 9193852-(4-Methylphenyl)-1,3-benzothiazole

Product 1

HCID 132767292-(4-(Bromomethyl)phenyl)benzo[d]thiazoleYield 67.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 45 g (0.2 mol) of 4-(benzothiazol-2-yl) toluene in 1000 ml of dry carbon tetrachloride were added 35.6 g (0.2 mol) of N-bromosuccinimide and a catalytic amount of benzoyl peroxide. The mixture was refluxed for 12 hours, and then allowed to cool down to room temperature. The precipitated succinimide was filtered off and the filtrate evaporated to dryness in vacuo, whereupon 55 g of crude crystals were obtained. Recrystallization from 1500 ml of cyclohexane gave 41 g of purified 4-(benzothiazol-2-yl) bromomethylbenzene as colorless flakes.

Workup

  1. temperatureThe mixture was refluxed for 12 hours
  2. filtrationThe precipitated succinimide was filtered off
  3. customthe filtrate evaporated to dryness in vacuo, whereupon 55 g of crude crystals
  4. customwere obtained
  5. customRecrystallization from 1500 ml of cyclohexane

Sources & evidence

ORD record
ord-d62e145b728e4e42b4ad7a36cfd34c4b
Source dataset
uspto-grants-1980_11
Patent number
US04232010

Reaction notes

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