Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (E)-ethyl 3-(5-bromo-2-chloropyridin-3-yl)acrylate

HRID 1504532Notes

Reaction equation

HRID 1504532 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH:7]=O.[C:11]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:13][CH2:14][CH3:15])=[O:12]>C1COCC1>[Br:1][C:2]1[CH:9]=[C:6](/[CH:7]=[CH:16]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]([Cl:10])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 230909885-Bromo-2-chloropyridine-3-carbaldehyde

Product 1

HCID 117749056(E)-ethyl 3-(5-bromo-2-chloropyridin-3-yl)acrylateYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A vial was charged with 5-bromo-2-chloronicotinaldehyde (500 mg, 2.268 mmol, Small Molecules, Inc.) and THF (9072 μl). (Carbethoxymethylene)triphenylphosphorane (830 mg, 2.381 mmol) was added to the solution, and the mixture was stirred at RT for 1.5 h. The crude mixture was loaded onto silica gel and purified using a gradient of 0-50% EtOAc/heptane to provide (E)-ethyl 3-(5-bromo-2-chloropyridin-3-yl)acrylate (660 mg, 2.272 mmol, 100% yield) as a white solid. m/z (ESI) 291.8 (M+H)+.

Workup

  1. custompurified

Sources & evidence

ORD record
ord-87021d8abc274a04aca23a3f4299265b
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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