Triphenylphosphine → ((5-Phenylpyridin-2-yl)-methyl)triphenylphosphonium bromide

HRID 1084428Notes

Reaction equation

HRID 1084428 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][N:4]=1.[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CC#N>[Br-:1].[C:9]1([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][P+:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:4][CH:5]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 151713012-(Bromomethyl)-5-phenylpyridine

Product 1

HCID 19769458((5-Phenylpyridin-2-yl)-methyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To the bromide (step 2) (100 mg) in CH3CN (2 cc) was added triphenylphosphine (400 mg) and the mixture was heated at 70° C. for 1.5 hours. The solvent was removed in vacuo and replaced by Et2O (3 cc) and toluene (3 cc). The resulting solid was swished for 3 hours, filtered and dried to afford the title compound, used as such in the next step.

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-d1a607fcef144dde851344aedfa321bb
Source dataset
uspto-grants-1991_04
Patent number
US05004743

Reaction notes

Loading…