Triphenylphosphine → 4-Trifluoromethoxybenzyltriphenylphosphonium bromide

HRID 1084789Notes

Reaction equation

HRID 1084789 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][Br:9])=[CH:6][CH:5]=1.[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[Br-:9].[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][P+:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzene

Product 1

HCID 224076584-Trifluoromethoxybenzyltriphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(trifluoromethoxy)benzyl bromide (5.3 g) and triphenylphosphine (5.42 g) in acetonitrile (100 ml) was heated under reflux for 12h. The acetonitrile was evaporated under reduced pressure, and ethyl acetate (50 ml) was added to the residue. The solid material so obtained was filtered off, washed with ethyl acetate (100 ml) and dried, to give (4-trifluoromethoxybenzyl)triphenyl phosphonium bromide, N.M.R. in d6 -dimethylsulphoxide: δ5.2 (2H,d), 7.1 (2H,2d), 7.25 (2H,d), 7.8 (9H,m).

Workup

  1. temperatureunder reflux for 12h
  2. customThe acetonitrile was evaporated under reduced pressure, and ethyl acetate (50 ml)
  3. additionwas added to the residue
  4. customThe solid material so obtained
  5. filtrationwas filtered off
  6. washwashed with ethyl acetate (100 ml)
  7. customdried

Sources & evidence

ORD record
ord-5f22f492492b4eb28d77668775f8e32d
Source dataset
uspto-grants-1991_04
Patent number
US05006543

Reaction notes

Loading…