4-Nitrobenzyl chloride → 4-Nitrobenzyltriphenylphosphonium chloride

HRID 1955678Notes

Reaction equation

HRID 1955678 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][Cl:28])=[CH:25][CH:24]=1)([O-:22])=[O:21]>CC#N.CCOCC>[Cl-: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

5

Reactant 2

HCID 74824-Nitrobenzyl chlorideHCID 11776Triphenylphosphine

Product 1

HCID 120003154-Nitrobenzyltriphenylphosphonium chlorideYield 84.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Triphenylphosphine (38.17 g, 0.146 mole) and 4-nitrobenzyl chloride (25g, 0.146 mole) were dissolved in CH3CN (100 mL) and heated at reflux for 2 hours, and then allowed to cool to room temperature. The reaction mixture was diluted with Et2O (300 mL), the white solid was filtered, washed with Et2O (200 mL), and dried in vacuo, giving 53.3 g (84%) of 4-nitrobenzyltriphenylphosphonium chloride as a single spot on TLC: (Rf =0.71, 4:1:1 butanol:acetic acid:water). 1H-NMR (d6 -DMSO): 5.40-5.50 (2H, d, CH2P, J=20 Hz); 7.20-7.40 (2H, dd, aromatic); 7.40-7.80 (12H, m, aromatic); 7.90-8.00 (3H, m, aromatic); 8.10-8.20 (2H, d, aromatic).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. filtrationthe white solid was filtered
  4. washwashed with Et2O (200 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-45958cecdee14b1a8e34abe8eb540042
Source dataset
uspto-grants-1998_07
Patent number
US05776718

Reaction notes

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