Triphenylphosphine → (3-Cyanobenzyl)triphenylphosphonium bromide

HRID 2074295Notes

Reaction equation

HRID 2074295 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.[C:20]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][Br:26])#[N:21]>>[Br-:26].[C:20]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)#[N:21]

Participants

3

Reactant 2

HCID 11776TriphenylphosphineHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 2778355(3-Cyanobenzyl)triphenylphosphonium bromideYield 72.7%

Conditions

Temperature
80 °C

Procedure

Triphenylphosphine (2.8 g) was added to a Tol (50 ml) solution of 3-cyanobenzyl bromide (2.0 g), followed by stirring at 80° C. for 5 hours. This was cooled to room temperature, and the precipitated solid was collected by filtration, and washed with Tol. This was dried under reduced pressure to obtain (3-cyanobenzyl)(triphenyl)phosphonium bromide (3.4 g).

Workup

  1. temperatureThis was cooled to room temperature
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with Tol
  4. customThis was dried under reduced pressure

Sources & evidence

ORD record
ord-e6981f8b05c24ed29dc9eee5ea77fd05
Source dataset
uspto-grants-2011_04
Patent number
US07919495B2

Reaction notes

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