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

HRID 628624Notes

Reaction equation

HRID 628624 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-50f3e513b31d40519d24bd0b1809596c
Source dataset
uspto-grants-2016_04
Patent number
US09314467B2

Reaction notes

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