1,2-Dimethoxyethane → 2-(4-Bromophenyl)thiophene-3-carbonitrile

HRID 1865042Notes

Reaction equation

I[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]#[N: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[C:7]#[N:8])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-iodothiophene-3-carbonitrile (20 g, 85 mmol, preparation 23), 4 bromobenzeneboronic acid (18.8 g. 94 mmol), potassium carbonate (26 g, 187 mmol) and tetrakis(triphenylphosphine)-palladium (0) (10 g, 8.5 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 material is purified by column chromatography (hexane-ethyl acetate 10/1) to provide the title compound as a white solid. 1H NMR (CDCl3): 7.32 (m, 2H), 7.62 (m, 4H).

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 material is purified by column chromatography (hexane-ethyl acetate 10/1)

Sources & evidence

ORD record: ord-0f92c7ef215e4f239ddb7c25c4b440b8
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625932B2

Reaction notes

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