Benzoyl Peroxide → 6-Bromomethyl-3-chloro-2-methoxycarbonylbenzo[b]thiophene

HRID 1682561Notes

Reaction equation

HRID 1682561 reaction equation
[Cl:1][C:2]1[C:3]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].C1C(=O)N([Br:23])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC1C=CC=CC=1.CC(=O)OCC>[Br:23][CH2:15][C:12]1[CH:13]=[CH:14][C:3]2[C:2]([Cl:1])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[S:5][C:4]=2[CH:11]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 4154210Methyl 3-chloro-6-methylbenzo(b)thiophene-2-carboxylate

Product 1

HCID 136629866-Bromomethyl-3-chloro-2-methoxycarbonylbenzo[b]thiopheneYield 68.6%

Reagents, catalysts & solvents 2

HCID 7964ChlorobenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.5 g (10.4 mmol) of 3-chloro-2-methoxycarbonyl-6-methylbenzo[b]thiophene (prepared according to J. Org. Chem. 41, 3399 (1976)) are boiled under reflux in 150 ml of chlorobenzene with 1.87 g of NBS and 420 mg of dibenzoyl peroxide for 5 h. After distilling off the chlorobenzene in a rotary evaporator, the residue obtained is taken up in EA, and the EA solution is washed with satd. NaHCO3 solution, 10% strength Na2SO3 solution and satd. NaCl solution, dried over Na2SO4 and concentrated. Chromatography on SiO2 using EA/Hep 1:20 yields 2.28 g of the title compound.

Workup

  1. distillationAfter distilling off the chlorobenzene
  2. customin a rotary evaporator
  3. customthe residue obtained
  4. washthe EA solution is washed with satd
  5. dry with materialNaCl solution, dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-22067db8e9e94e29b4cccca87cb4e0ad
Source dataset
uspto-grants-1997_06
Patent number
US05635525

Reaction notes

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