Triphenylphosphine → [(4-Nitrophenyl)methyl](triphenyl)phosphanium bromide

HRID 2086595Notes

Reaction equation

HRID 2086595 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27][Br:28])=[CH:25][CH:24]=1)([O-:22])=[O:21]>C(Cl)Cl>[Br-:28].[N+:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27][P+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:25][CH:24]=1)([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 197008[(4-Nitrophenyl)methyl](triphenyl)phosphanium bromideYield 115.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of triphenylphosphine (25.92 g) in 300 mL CH2Cl2 is added 4-nitrobenzylbromide (31.47 g). The solution is allowed to stir overnight. The mixture is concentrated. The resulting solid is triturated with Et2O, filtered and dried to yield 54.58 g (95%) of the desired product as a white solid.

Workup

  1. concentrationThe mixture is concentrated
  2. customThe resulting solid is triturated with Et2O
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-eefe74aed8d142559a37515da233ca70
Source dataset
uspto-grants-2004_04
Patent number
US06727248B2

Reaction notes

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