4-Methoxyphenol → 3-(4-Methoxyphenoxy)benzo[b]thiophene

HRID 1386984

Reaction equation

Br[C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.[Cu]I>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:2]2[C:3]3[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=3[S:5][CH:6]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 4.00 g (19.7 mmol) of 3-bromobenzo[b]thiophene, 4.96 g (40 mmol) of 4-methoxyphenol, 5.52 g (40 mmol) of K2CO3, and 0.20 g (1.0 mmol) of CuI was heated to 140° C. and sonicated at this temperature for 2 h. The reaction was allowed to cool, taken up in CH2Cl2, and the mixture was washed several times with 0.5 N NaOH. The organic layer was dried over Na2SO4 and concentrated in vacuo to an oil that was subjected to chromatography (SiO2; gradient of 0-5% EtOAc in hexanes). The fractions containing the desired product were combined, evaporated in vacuo, and the residue was recrystallized from hexanes to afford 500 mg (1.95 mmol; 10%) of the title compound as a white solid.

Workup

customsonicated at this temperature for 2 h
temperatureto cool
washthe mixture was washed several times with 0.5 N NaOH
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo to an oil that
additionThe fractions containing the desired product
customevaporated in vacuo
customthe residue was recrystallized from hexanes

Sources & evidence

ORD record: ord-88fa74840acb457dbd2585d04240b8d3
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265575B1

Linked notes

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