Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 3-(6-Bromopyridin-3-yl)acrylic acid methyl ester

HRID 238306Notes

Reaction equation

HRID 238306 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br:25][C:26]1[N:31]=[CH:30][C:29]([CH:32]=O)=[CH:28][CH:27]=1>C1COCC1>[CH3:1][O:2][C:3](=[O:24])[CH:4]=[CH:32][C:29]1[CH:30]=[N:31][C:26]([Br:25])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 714275823-(6-Bromopyridin-3-yl)acrylic acid methyl esterYield 90.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20 g (59.8 mmol) of 2-(triphenylphosphoranylidene)acetic acid methyl ester were added, by portion, to a solution of 11.1 g (59.8 mmol) of 6-bromopyridine-3-carbaldehyde in anhydrous THF at 0° C. The mixture was stirred at 0° C. to room temperature for 4 h. The solvent was removed in vacuo and the residue was purified by chromatography (silica gel, cyclohexane/ethyl acetate 95:5) to give 13.1 g (90.4%) of the title compound (trans/cis ratio 95:5) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by chromatography (silica gel, cyclohexane/ethyl acetate 95:5)

Sources & evidence

ORD record
ord-6e25989d1f154dda99f1e1a3990c1631
Source dataset
uspto-grants-2014_02
Patent number
US08642620B2

Reaction notes

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