Bromine → 3-Bromo-5-chlorobenzo[b]thiophene

HRID 2206817Notes

Reaction equation

HRID 2206817 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.C([O-])(=O)C.[Na+].[Br:16]Br.S(=O)(=O)(O)[O-].[Na+]>ClCCl>[Br:16][C:7]1[C:6]2[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[S:9][CH:8]=1

Participants

6

Reactant 4

HCID 24408BromineHCID 516919Sodium BisulfateHCID 517045Sodium AcetateHCID 113097545-Chlorobenzo(b)thiophene

Product 1

HCID 142423383-Bromo-5-chlorobenzo[b]thiopheneYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 250 mL 2-neck round flask, 5-chlorobenzothiophene (2 g, 11.8 mmol) was dissolved in dichloromethane (10 mL), and sodium acetate (NaOAc) (1.95 g, 23.6 mmol) and Br2 (1.89 g, 11.8 mmol) were gradually added to the mixture for 5 minutes at 0□. After the reaction, a 10% sodium bisulfate (NaHSO3) solution (20 mL) was poured to the mixture, and then the resulting mixture was extracted with ethyl acetate (20 mL), dried over MgSO4, and distilled in vacuum to give 2.49 g of yellow solid (85% yield).

Workup

  1. customAfter the reaction
  2. extractionthe resulting mixture was extracted with ethyl acetate (20 mL)
  3. dry with materialdried over MgSO4
  4. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-229e0f52596343c4b41ae8730fea62b1
Source dataset
uspto-grants-2016_06
Patent number
US09373794B2

Reaction notes

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