Benzo(B)Thiophene → Benzo(b)thiophene, 3-bromo-

HRID 2220006Notes

Reaction equation

HRID 2220006 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.[Br:10]Br>C(Cl)(Cl)Cl>[Br:10][C:4]1[C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[S:1][CH:5]=1

Participants

4

Reactant 2

HCID 7221Benzo(B)ThiopheneHCID 24408Bromine

Product 1

HCID 123250Benzo(b)thiophene, 3-bromo-Yield 85.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of 6 g (0.044 mol) of Benzo[b]thiophene and 80 mL of CHCl3. is cooled by using an ice-water bath. A solution of 7.89 g (0.044 mol) of Br2 and 40 mL of CHCl3 is added slowly. After the addition is completed, the mixture is stirred for 1 h at room temperature and then hydrolysed with 150 mL of saturated aqueous Na2S2O6 solution. The aqueous phase is extracted two times with 150 mL of CHCl3. The combined organic phases are washed several times with water, dried over magnesium sulfate and then are concentrated under reduced pressure. The crude product is purified by distillation to give a colourless liquid (8.0 g, 84% yield).

Workup

  1. temperatureis cooled
  2. additionAfter the addition
  3. extractionThe aqueous phase is extracted two times with 150 mL of CHCl3
  4. washThe combined organic phases are washed several times with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationare concentrated under reduced pressure
  7. distillationThe crude product is purified by distillation

Sources & evidence

ORD record
ord-e55916e356a54d61890a959e215ead5d
Source dataset
uspto-grants-2008_08
Patent number
US07416682B2

Reaction notes

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