Triphenylphosphine → 3-Trifluoromethylsulfonyloxy-4-methoxycarbonylbenzyl triphenylphosphonium bromide

HRID 2228013Notes

Reaction equation

HRID 2228013 reaction equation
[Br:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([O:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])[CH:4]=1.[C:21]1([P:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[Br-:1].[F:18][C:17]([F:20])([F:19])[S:14]([O:13][C:5]1[CH:4]=[C:3]([CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])[CH2:2][P+:27]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 18474595Methyl 4-bromomethyl-2-trifluoromethylsulfonyloxybenzoate

Product 1

HCID 867583153-Trifluoromethylsulfonyloxy-4-methoxycarbonylbenzyl triphenylphosphonium bromideYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 4-bromomethyl-2-trifluoromethylsulfonyloxybenzoate (23.12 g; 61 mmol) and triphenylphosphine (16 g; 61 mmol) in toluene (240 ml) was refluxed for 5 hours. The resulting solid was filtered and washed with ether to give 3-trifluoromethylsulfonyloxy-4-methoxycarbonylbenzyl triphenylphosphonium bromide. Yield=100%.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with ether

Sources & evidence

ORD record
ord-96b941c0e505453792bb3c35a018cb81
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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