Tri(butyl)vinyltin → 5-(4-Chloro-phenyl)-3-vinyl-thiophene-2-carboxylic acid methyl ester

HRID 2384863Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:8][C:9]=1Br)=[O:4].[CH2:18](C([Sn])=C(CCCC)CCCC)[CH2:19]CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:8][C:9]=1[CH:18]=[CH2:19])=[O:4]

Participants

Conditions

Temperature: 110 °C

Procedure

Dissolve 3-bromo-5-(4-chloro-phenyl)-thiophene-2-carboxylic acid methyl ester (570 mg, 1.72 mmol) in toluene (10 mL) and add tributylvinyltin (0.55 mL, 1.89 mmol), and tetrakis(triphenylphosphine)palladium (40 mg, 0.034 mmol). Heat the mixture to 110° C. for 17 h. Cool the mixture to room temperature and concentrate in vacuo. Purify by chromatography eluting with 5% ethyl acetate/hexane to give 0.37 g (77%) of the title compound. LC-MS/ES m/z (35Cl) 279.0 [M+H]−.

Workup

temperatureCool the mixture to room temperature
concentrationconcentrate in vacuo
customPurify by chromatography
washeluting with 5% ethyl acetate/hexane

Sources & evidence

ORD record: ord-8cffe4e98dd6455b813cca26ad400e7d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263772B2

Reaction notes

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