Bromine → 3-Bromo-6-methoxy-2-(4-methoxyphenyl)-benzo[b]thiophene

HRID 1954181Notes

Reaction equation

HRID 1954181 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]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.[Br:20]Br>C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[Br:20])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene

Product 1

HCID 8509423-Bromo-6-methoxy-2-(4-methoxyphenyl)-benzo[b]thiopheneYield 99.8%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

A slurry of 2-(4-methoxyphenyl)-6-methoxybenzo[b]thiophene 100 g (370 mmol) in 1 L of CHCl3 was heated to reflux then removed from the heat. A solution of 19.3 mL (370 mmol) of bromine in 170 mL of carbon tetrachloride was added dropwise as the solution slowly cooled to room temperature. The resulting mixture was concentrated to dryness in vacuo to yield 129 g of the title compound as brown solid.

Workup

  1. temperatureto reflux
  2. customthen removed from the heat
  3. concentrationThe resulting mixture was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-2d634866cfcc482c8424be4ba3d19500
Source dataset
uspto-grants-2000_09
Patent number
US06121293

Reaction notes

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