Bromine → 3-Bromo-2-(4-methoxyphenyl)benzo[b]thiophene

HRID 1386982Notes

Reaction equation

HRID 1386982 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.[Br:18]Br>C(Cl)(Cl)Cl>[Br:18][C:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[S:13][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 41373912-(4-Methoxyphenyl)benzothiophene

Product 1

HCID 105436263-Bromo-2-(4-methoxyphenyl)benzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A slurry of 5.0 g (20.8 mmol) of 2-(4-methoxyphenyl)benzo[b]thiophene (Example 3, Part A) in 400 mL of CHCl3 at 0° C. was treated slowly with 1.6 mL of Br2, resulting in a yellow solution. The reaction was stirred at 0° C. for 1 h and then washed sequentially with 200 mL of 1.0 N aq Na2S2O3, 200 mL of 1.0 N aq NaHCO3, and 200 mL of H2O. After drying over Na2SO4, evaporation of the solvent in vacuo gave 6.24 g (19.5 mmol; 94%) of an off-white solid which was clean by thin layer chromatography.

Workup

  1. customresulting in a yellow solution
  2. washwashed sequentially with 200 mL of 1.0 N aq Na2S2O3, 200 mL of 1.0 N aq NaHCO3, and 200 mL of H2O
  3. dry with materialAfter drying over Na2SO4, evaporation of the solvent in vacuo
  4. customgave 6.24 g (19.5 mmol; 94%) of an off-white solid which

Sources & evidence

ORD record
ord-260baaf542c2427abf26d67d500e5fc4
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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