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

HRID 234700Notes

Reaction equation

HRID 234700 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)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 48,408%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

Dissolve benzo[b]thiophene (23g, 0.170mmol) in carbon tetrachloride (80mL). Add, by dropwise addition, a solution of bromine (26.85g, 0.168mmol) in carbon tetrachloride (30mL) and stir at room temperature for 2 days. Quench with a 1M solution of sodium thiosulfate and separate the organic phase. Extract the aqueous phase with carbon tetrachloride, combine the organic phases and dry (MgSO4). Evaporate the solvent in vacuo and purify by distillation to give 3-bromobenzo[b]thiophene as a pale yellow liquid (17.33g, 48%); bp 64°-72° [email protected] Hg.

Workup

  1. additionAdd, by dropwise addition
  2. customQuench with a 1M solution of sodium thiosulfate
  3. customseparate the organic phase
  4. extractionExtract the aqueous phase with carbon tetrachloride
  5. dry with materialdry (MgSO4)
  6. customEvaporate the solvent in vacuo
  7. distillationpurify by distillation

Sources & evidence

ORD record
ord-ca2f65c1f4c94ef4be57b86f7d77fe73
Source dataset
uspto-grants-1997_01
Patent number
US05596003

Reaction notes

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