Triphenylphosphine → {2-[Difluoro-(4'-trifluoromethylbiphenyl-4-yl)methoxy]-5-fluorobenzyl}triphenylphosphonium bromide

HRID 1672640Notes

Reaction equation

HRID 1672640 reaction equation
[F:1][C:2]([O:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[CH2:28][Br:29])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[C:30]1([P:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[Br-:29].[F:1][C:2]([F:19])([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[O:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[CH2:28][P+:36]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 578643902-(Bromomethyl)-4-fluorophenyl difluoro[4'-(trifluoromethyl)biphenyl-4-yl]methyl ether

Product 1

HCID 86634288{2-[Difluoro-(4'-trifluoromethylbiphenyl-4-yl)methoxy]-5-fluorobenzyl}triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

217 mg (0.46 mmol) of 2-(bromomethyl)-4-fluorophenyl difluoro[4′-(trifluoromethyl)biphenyl-4-yl]methyl ether from Example 41A and 148 mg (0.57 mmol) of triphenylphosphine are stirred in 5 ml of THF at RT for 12 hours. The reaction mixture is concentrated and the residue is washed with diethyl ether and n-hexane. The crude product is employed without further purification in the subsequent stage.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. washthe residue is washed with diethyl ether and n-hexane
  3. customThe crude product is employed without further purification in the subsequent stage

Sources & evidence

ORD record
ord-aabdb13b7a90497f99e58e99c5a2e1ab
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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