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

HRID 2306645Notes

Reaction equation

HRID 2306645 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(O)(=O)C>[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 94.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

Benzothiophene (2.68 g, 20.0 mmol) was dissolved in glacial acetic acid (100 mL) and cooled to 0° C. The resulting solution was treated by dropwise addition of bromine (1.08 mL, 21.0 mmol). The reaction mixture was allowed to warm to room temperature and was stirred for 16 hours. The crude mixture was concentrated to an oil. The residue was purified by silica gel chromatography eluting with hexane to obtain 4.02 g (94%) 3-bromobenzothiophene.

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe crude mixture was concentrated to an oil
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with hexane

Sources & evidence

ORD record
ord-42ac63843e66403086e60e2e171e2ea0
Source dataset
uspto-grants-2004_12
Patent number
US06828332B1

Reaction notes

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