Bromoacetonitrile → (Triphenylphosphoranylidene)acetonitrile

HRID 705797Notes

Reaction equation

HRID 705797 reaction equation
Br[CH2:2][C:3]#[N:4].[C:5]1([P:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(OCC)(=O)C>[C:18]1([P:11]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:2][C:3]#[N:4])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 11534BromoacetonitrileHCID 11776Triphenylphosphine

Product 1

HCID 85524(Triphenylphosphoranylidene)acetonitrileYield 125.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of bromoacetonitrile (26.2 g, 218 mmol) and triphenylphosphine (52.0 g, 198 mmol) in ethyl acetate (240 mL) was stirred at 85° C. overnight, filtered and washed with petroleum ether. The filtrated cake was dried in air to give the title compound as a white solid (75 g), which was used without further purification. LCMS: rt=0.95 min, [M+H+]=302

Workup

  1. filtrationfiltered
  2. washwashed with petroleum ether
  3. customThe filtrated cake was dried in air

Sources & evidence

ORD record
ord-06a23f9ee23b4278a04fb1e9f9c5a9c6
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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