tert-Butyl (triphenylphosphoranylidene) acetate → Tert-butyl 3-(6-bromo-2-methoxypyridin-3-yl)acrylate

HRID 70553Notes

Reaction equation

HRID 70553 reaction equation
[C:1]([O:5][C:6]([CH:8]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[C:31]([O:37][CH3:38])[N:30]=1>C(Cl)(Cl)Cl>[Br:28][C:29]1[N:30]=[C:31]([O:37][CH3:38])[C:32]([CH:33]=[CH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetateHCID 122692136-Bromo-2-methoxynicotinaldehyde

Product 1

HCID 86658007Tert-butyl 3-(6-bromo-2-methoxypyridin-3-yl)acrylateYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(tert-Butoxycarbonylmethylene)triphenylphosphorane (1.74 g) was added to a solution of 6-bromo-2-methoxynicotinaldehyde (500 mg) in chloroform (5 mL) under ice-cooling, followed by stirring for one hour. The solvent was evaporated from the reaction solution under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give tert-butyl 3-(6-bromo-2-methoxypyridin-3-yl)acrylate as a colorless oil (726 mg, 100%).

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated from the reaction solution under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-0d67ace4cd5b44c18847e836ae37bb44
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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