Water → 4-[2-Bromo-2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde

HRID 2375544Notes

Reaction equation

HRID 2375544 reaction equation
P(Br)(Br)[Br:2].[CH2:5]([C:7]1[CH:8]=[CH:9][C:10]([CH:13](O)[CH2:14][O:15][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=2)=[N:11][CH:12]=1)[CH3:6].O>C(Cl)(Cl)Cl>[Br:2][CH:13]([C:10]1[CH:9]=[CH:8][C:7]([CH2:5][CH3:6])=[CH:12][N:11]=1)[CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 115507874-[2-(5-Ethyl-2-pyridinyl)-2-hydroxyethoxy]benzaldehyde

Product 1

HCID 713792484-[2-Bromo-2-(5-ethylpyridin-2-yl)ethoxy]benzaldehydeYield 89.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.93 g (0.01 mol) PBr3 was added to a solution of 5 g (0.018 mol) 4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxy-ethoxy]-benzaldehyde dissolved in 50 mL chloroform at 55-60° C. Reaction mixture was refluxed for 1 hr. Progress of the reaction was monitored by TLC and after completion of reaction, subsequent work-up in alkaline water furnished 3 g (50%) of desired product.

Workup

  1. customReaction mixture
  2. temperaturewas refluxed for 1 hr

Sources & evidence

ORD record
ord-8f738486fbe64a849be63842c96835e5
Source dataset
uspto-grants-2008_12
Patent number
US07465801B2

Reaction notes

Loading…