p-Toluenesulfonic acid → 2-Bromo-6-methoxybenzo[b]thiophene

HRID 1453906

Reaction equation

HRID 1453906 reaction equation
[Br:1]N1C(=O)CCC1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:25]2[CH:26]=[CH:27][S:28][C:24]=2[CH:23]=1>ClCCCl>[Br:1][C:27]1[S:28][C:24]2[CH:23]=[C:22]([O:21][CH3:20])[CH:30]=[CH:29][C:25]=2[CH:26]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 67184N-bromobutanimideHCID 136342376-Methoxy-1-benzothiophene

Product 1

HCID 235129022-Bromo-6-methoxybenzo[b]thiopheneYield 82.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

N-bromosuccinimide (14.70 g, 82.59 mmol) and p-toluenesulfonic acid (2.70 g, 15.68 mmol) were added to a solution of benzothiophene (3) (15.10 g, 92.07 mmol) in 1,2-dichloroethane (300 ml). The mixture was maintained at 70° C. for 35 min, cooled in an ice bath, and the succinimide was removed by filtration. The solution was extracted with saturated sodium bicarbonate solution, dried over Na2SO4, filtered, and concentrated under vacuum to give 22.00 g as an oil. Crystallisation from pentane afforded a white solid (16.50 g, 74%), mp 62° C.

Workup

  1. temperaturecooled in an ice bath
  2. customthe succinimide was removed by filtration
  3. extractionThe solution was extracted with saturated sodium bicarbonate solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto give 22.00 g as an oil
  8. customCrystallisation from pentane

Sources & evidence

ORD record
ord-77fd94c4c66d4329b9c479b4e8728942
Source dataset
uspto-grants-2009_01
Patent number
US07476691B2

Linked notes

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