Diethyl Ether → Isobutylcarbonylmethyltriphenylphosphonium bromide

HRID 1733823Notes

Reaction equation

HRID 1733823 reaction equation
[Br:1][CH2:2][C:3]([CH2:5][CH:6]([CH3:8])[CH3:7])=[O:4].[C:9]1([P:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCOCC>C(Cl)Cl>[Br-:1].[CH2:5]([C:3]([CH2:2][P+:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:4])[CH:6]([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 110844641-Bromo-4-methyl-2-pentanone

Product 1

HCID 22914202Isobutylcarbonylmethyltriphenylphosphonium bromideYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromomethylisobutyl ketone (53.6 g) and triphenylphosphine (78.5 g) are intimately mixed in a 500 ml round-bottom flask and, after the initially strong heat tonality subsides, are left for 12 hours under nitrogen at room temperature. After that, the solid reaction mass is taken up in 330 ml of methylene chloride and refluxed for 30 minutes. After adding 500 ml of ether, it is allowed to cool to room temperature and the product is isolated by filtration. After drying,111.7 g of the phosphonium salt with a melting point of 244-245° C. is obtained.

Workup

  1. customAfter that, the solid reaction mass
  2. temperaturerefluxed for 30 minutes
  3. customthe product is isolated by filtration
  4. customAfter drying

Sources & evidence

ORD record
ord-2a5c7987061c4020a8608ccad01cf1c6
Source dataset
uspto-grants-1996_07
Patent number
US05532228

Reaction notes

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