Benzoyl Peroxide → 4-Bromo-5-(bromomethyl)-2-methyl-1,3-benzothiazole

HRID 1192464Notes

Reaction equation

HRID 1192464 reaction equation
[Br:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.ClCCl>[Br:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][Br:13]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 672576564-Bromo-2,5-dimethyl-1,3-benzothiazole

Product 1

HCID 672574674-Bromo-5-(bromomethyl)-2-methyl-1,3-benzothiazoleYield 74%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-bromo-2,5-dimethyl-1,3-benzothiazole (5.8 g, 24 mmol), N-bromosuccinimide (5.12 g, 28.7 mmol), and benzoyl peroxide (0.580 g, 2.40 mmol) in carbon tetrachloride (100 mL) was heated at reflux overnight. The mixture was diluted with dichloromethane, washed with 1 N NaOH, brine and dried over sodium sulfate, then concentrated under reduced pressure. The residue was purified on silica gel, eluting with 0% to 50% EtOAc in hexane, to give the desired product (5.70 g, 74%). LCMS calculated for C9H8Br2NS(M+H)÷: m/z=319.9; found: 319.8.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. washwashed with 1 N NaOH, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified on silica gel
  7. washeluting with 0% to 50% EtOAc in hexane

Sources & evidence

ORD record
ord-7a30045f109444ac84bfe3742dba7a82
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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