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

HRID 2305301Notes

Reaction equation

HRID 2305301 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[S:8][C:7]=2[CH:19]=1.[Br:20]Br>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([Br:20])=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)[S:8][C:7]=2[CH:19]=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 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene (27.0 g, 100 mmol)in 1.10 L of CHCl3 at 60° C. was added bromine (15.98 g, 100 mmol) dropwise as a solution in 200 mL of CHCl3. 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 6-methoxy-2-(4-methoxyphenyl)-3-bromobenzo[b]thiophene as a white solid. mp 83-85 OC. 1H NMR (DMSO-d6) δ 7.70-7.62 (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 C16H13O2SBr: 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-61381402214348e58da97fc44c904538
Source dataset
uspto-grants-2002_08
Patent number
US06440958B1

Reaction notes

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