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

HRID 1421391Notes

Reaction equation

HRID 1421391 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>[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

4

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 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2-(4-methoxyphenyl)-6-methoxybenzo[b]thiophene (27.0 g, 100 mmol)in 1.10 L of chloroform at 60° C. was added bromine (15.98 g, 100 mmol) dropwise dissolved in 200 mL of chloroform. After the addition was complete, the reaction was cooled to room temperature, and the solvent removed in vacuo to provide 34.2 g (100%) of 2-(4-methoxyphenyl)-3-bromo-6-methoxybenzo[b]thiophene as a white solid. mp 83-85° C. 1H NMR (DMSO-d6) δ7.70-7.62 (m, 4H), 7.17 (dd, J=8.6, 2.0 Hz, 1H), 7.09 (d, J=8.4 Hz, 2H). FD mass spec: 349, 350. Anal. Calcd. for C16H13BrO2S: C, 55.03; H, 3.75. Found: C, 54.79; H, 3.76.

Workup

  1. additionAfter the addition
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-216685e76dc04088aefff5c74e0092cd
Source dataset
uspto-grants-2000_06
Patent number
US06075151

Reaction notes

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