1,2-Dimethoxyethane → HCID 57975385, compound

HRID 1865034Notes

Reaction equation

I[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[S:7][CH3:8].[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].C(COC)OC>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[S:3][CH:4]=[CH:5][C:6]=2[S:7][CH3:8])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-iodo-3-methylthiothiophene (18 g, 70.3 mmol, preparation 2), 4 bromobenzeneboronic acid (14.1 g, 70.3 mmol), potassium carbonate (21.4 g, 155 mmol), tetrakis(triphenylphosphine)-palladium (0) (8.1 g, 7.02 mmol) in a mixture of anhydrous dimethoxyethane (300 ml) and absolute ethanol (150 ml) is degassed with Ar or N2 for 15 min and stirred for 12 hours at 80° C. The reaction mixture is cooled to room temperature, water (100 ml) is then added and the crude product is extracted with methylene chloride (3×150 ml). The crude product is purified by column chromatography using hexane as eluent solvent yielding 12 g (60%) of title compound as a white solid. NOTE: This product is also light sensitive and should be used immediately.

Workup

customis degassed with Ar or N2 for 15 min
temperatureThe reaction mixture is cooled to room temperature
additionwater (100 ml) is then added
extractionthe crude product is extracted with methylene chloride (3×150 ml)
customThe crude product is purified by column chromatography

Sources & evidence

ORD record: ord-c0a36ae5e19e46ccb9614538b10e6631
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625932B2

Reaction notes

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