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

HRID 542769Notes

Reaction equation

HRID 542769 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[Br:10]Br>C(Cl)(Cl)(Cl)Cl>[Br:10][C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][CH:2]=1

Participants

4

Reactant 2

HCID 7221Benzo(B)ThiopheneHCID 24408Bromine

Product 1

HCID 123250Benzo(b)thiophene, 3-bromo-Yield 70.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 25 g of 1-benzothiophene in 100 ml of carbon tetrachloride at 15° C. were added 29.5 g of bromine over 6 hours. The reaction was allowed to stir at room temperature for 48 hours, at which time the reaction mixture was washed twice with a 1N aqueous sodium thiosulfate solution. The organic solution was dried over magnesium sulfate and evaporated to dryness. The resulting oil was vacuum distilled at 2 torr. Fractions collected between about 86°-90° L C. provided 27.7 g of the desired subtitle intermediate.

Workup

  1. washwas washed twice with a 1N aqueous sodium thiosulfate solution
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. customevaporated to dryness
  4. distillationdistilled at 2 torr
  5. customFractions collected between about 86°-90° L C

Sources & evidence

ORD record
ord-7e5729f93bb140f194c459d7b26db8d8
Source dataset
uspto-grants-1987_04
Patent number
US04659717

Reaction notes

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