Triphenylphosphine → 2,6-Bis(trifluoromethyl)benzyltriphenylphosphonium bromide

HRID 242720Notes

Reaction equation

HRID 242720 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[C:4]=1[CH2:5][Br:6].[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[Br-:6].[F:1][C:2]([F:16])([F:15])[C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[C:4]=1[CH2:5][P+:23]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 118513632,6-Bis(trifluoromethyl)benzyl bromide

Product 1

HCID 866321552,6-Bis(trifluoromethyl)benzyltriphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2,6-bis(trifluoromethyl)benzyl bromide (0.400 g, 1.30 mmol) in toluene (5 mL) was added triphenylphosphine (0.375 g, 1.43 mmol). The mixture was heated to reflux for 24 h. After cooling to room temperature, hexanes (10 mL) was added and the mixture was stirred for 1 h. The solid was collected by filtration and rinsed with hexanes to give 2,6-bis(trifluoromethyl)benzyltriphenylphosphonium bromide as a white solid. Yield (0.446 g, 60%): 1H NMR (400 MHz, DMSO-d6) δ 8.02 (d, J=8.0 Hz, 2H), 7.57-7.87 (m, 16H), 5.17 (d, J=15.2 Hz, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 h
  3. filtrationThe solid was collected by filtration
  4. washrinsed with hexanes

Sources & evidence

ORD record
ord-9e08f03df3cb42cb95afa06b3eb1623f
Source dataset
uspto-grants-2014_02
Patent number
US08653142B2

Reaction notes

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