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

HRID 2260123Notes

Reaction equation

HRID 2260123 reaction equation
[S:1]1[CH:5]=[C:4](C(C2CCN(C(OC(C)(C)C)=O)CC2)=O)[C:3]2[CH:21]=[CH:22][CH:23]=[CH:24][C:2]1=2.S1C=CC2C=CC=CC1=2.[Br:34]Br>C(Cl)(Cl)(Cl)Cl>[Br:34][C:4]1[C:3]2[CH:21]=[CH:22][CH:23]=[CH:24][C:2]=2[S:1][CH:5]=1

Participants

5

Reactant 3

HCID 7221Benzo(B)ThiopheneHCID 24408BromineHCID 153374564-[(Benzo[b]thiophene-3-yl)carbonyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester

Product 1

HCID 123250Benzo(b)thiophene, 3-bromo-Yield 48%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

4-[(Benzo[b]thiophene-3-yl)carbonyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester ##STR13## Dissolve benzo[b]thiophene (23 g, 0.170 mmol) in carbon tetrachloride (80 mL). Add, by dropwise addition, a solution of bromine (26.85 g, 0.168 mmol) in carbon tetrachloride (30 mL) 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 (17.33 g, 48%); bp 64°-72° C. @ 0.02 mm 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-8ea860528bc2449592281ceddc95dc08
Source dataset
uspto-grants-1995_12
Patent number
US05476861

Reaction notes

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