Diethyl Ether → HCID 86739169, compound

HRID 2295397Notes

Reaction equation

HRID 2295397 reaction equation
[CH3:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[N:4][C:5]([CH2:8][Br:9])=[CH:6][CH:7]=1.[C:16]1([P:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(OCC)C>CN(C)C=O>[Br-:9].[CH3:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[N:4][C:5]([CH:8]=[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]2[PH+:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 20475367HCID 20475367, compound

Product 1

HCID 86739169HCID 86739169, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.16 g (4.4 mmols) of 3-methyl-6-bromomethyl-2,2'-bipyridine together with 1.39 g (5.3 mmols) of triphenylphosphine in 50 ml of N,N-dimethylformamide are heated at 80° C. for 3 hours. At 23° C. and with rapid stirring, 50 ml of diethyl ether are added. The precipitating oily product crystallises after a short time and is filtered off with suction. After recrystallisation from 25 ml of water, 1.14 g (49% of theory) of [3-methyl-2,2'-bipyridin-6-yl-(methylene)]-triphenylphosphonium bromide are obtained in the form of colourless crystals; melting point 214°-215° C.

Workup

  1. customThe precipitating oily product crystallises after a short time
  2. filtrationis filtered off with suction
  3. customAfter recrystallisation from 25 ml of water, 1.14 g (49% of theory) of [3-methyl-2,2'-bipyridin-6-yl-(methylene)]-triphenylphosphonium bromide
  4. customare obtained in the form of colourless crystals

Sources & evidence

ORD record
ord-8f56b04995a64fc08b6d9ecd5b19022b
Source dataset
uspto-grants-1984_01
Patent number
US04424359

Reaction notes

Loading…