4-Bromothiophene-2-carbaldehyde → 3-(4-Bromo-thiophen-2-yl)-acrylic acid methyl ester

HRID 30291

Reaction equation

HRID 30291 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[S:5][CH:6]=1.[CH3:9][O:10][C:11](=[O:27])[CH2:12]P(OCC(F)(F)F)(OCC(F)(F)F)=O>>[CH3:9][O:10][C:11](=[O:27])[CH:12]=[CH:7][C:4]1[S:5][CH:6]=[C:2]([Br:1])[CH:3]=1

Participants

3

Reactant 2

HCID 877924-Bromothiophene-2-carbaldehydeHCID 184894Nsc 634137

Product 1

HCID 541625193-(4-Bromo-thiophen-2-yl)-acrylic acid methyl esterYield 78%

Procedure

4-Bromo-thiophene-2-carbaldehyde (44 g, 0.23 mol) and [Bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-acetic methyl ester (80.6 g, 0.253 mol) were treated by the method outlined in Example 34, step a) to afford the subtitle compound that was purified by column chromatography (SiO2) using a 0-60% ethylacetate-hexane gradient (46.22 g, yield: 78%). MS calculated for C8H7BrO2S+H: 247, observed: 247 249.

Sources & evidence

ORD record
ord-f2db750a4b23425ba000baac5c129435
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Linked notes

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