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

HRID 1013416Notes

Reaction equation

HRID 1013416 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-1fd42d6618164810a252529cc9390568
Source dataset
uspto-grants-2011_07
Patent number
US07981919B2

Reaction notes

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