Triphenylphosphine → (2-Fluoro-5-nitrobenzyl)(triphenyl)phosphonium bromide

HRID 85221Notes

Reaction equation

HRID 85221 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[F:12].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[Br-:1].[F:12][C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[CH2:2][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 103539672-(Bromomethyl)-1-fluoro-4-nitrobenzene

Product 1

HCID 86643536(2-Fluoro-5-nitrobenzyl)(triphenyl)phosphonium bromide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20 g (85.5 mmol) of the compound from Example 26A are dissolved in 250 ml of anhydrous toluene, and 22.4 g (85.5 mmol) of triphenylphosphine are added. The solution is heated under reflux for 16 h, resulting in the formation of a precipitate. The mixture is allowed to cool, and the precipitate is filtered off. After washing with diethyl ether, the precipitate is dried under reduced pressure. This gives 39 g (92% of theory) of the desired product.

Workup

  1. temperatureThe solution is heated
  2. temperatureunder reflux for 16 h
  3. customresulting in the formation of a precipitate
  4. temperatureto cool
  5. filtrationthe precipitate is filtered off
  6. washAfter washing with diethyl ether
  7. customthe precipitate is dried under reduced pressure

Sources & evidence

ORD record
ord-26f40b40097c47ada2414ad639ecf279
Source dataset
uspto-grants-2014_09
Patent number
US08846934B2

Reaction notes

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