Bromoacetonitrile → (Cyanomethyl)triphenylphosphonium bromide

HRID 899749Notes

Reaction equation

HRID 899749 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([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:3][CH:2]=1.[Br:20][CH2:21][C:22]#[N:23]>CCOCC>[Br-:20].[C:22]([CH2:21][P+:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)#[N:23]

Participants

4

Reactant 2

HCID 11534BromoacetonitrileHCID 11776Triphenylphosphine

Product 1

HCID 11811037(Cyanomethyl)triphenylphosphonium bromideYield 46%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of PPh3 (1.57 g, 5.99 mmol) in Et2O (30 mL) was added BrCH2CN (0.42 mL, 6.0 mmol). The reaction was stirred at reflux for 17 hours. The solvent was removed under reduced pressure, the residue was suction filtered from a small portion of ice-cold Et2O, and washed with a small amount of cold Et2O, giving the phosphonium salt as a white powder (1.05 g, 2.74 mmol, 46%). 1H NMR (CDCl3) δ 6.39 (d, 2H, J=15.3 Hz), 7.69-7.76 (m, 6H), 7.82-7.87 (m, 3H), 7.96-8.03 (m, 6H).

Workup

  1. temperatureat reflux for 17 hours
  2. customThe solvent was removed under reduced pressure
  3. filtrationfiltered from a small portion of ice-cold Et2O
  4. washwashed with a small amount of cold Et2O

Sources & evidence

ORD record
ord-475ac259f2b64ae0be174fa31dd75db0
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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