Diethyl Ether → {[2-(Methoxycarbonyl)phenyl]methyl}(triphenyl)phosphanium bromide

HRID 1160378Notes

Reaction equation

HRID 1160378 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25].C(OCC)C>C(#N)C>[Br-:20].[CH3:27][O:26][C:24]([C:23]1[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=1[CH2:21][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:25]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 2734813Methyl 2-(bromomethyl)benzoate

Product 1

HCID 10743695{[2-(Methoxycarbonyl)phenyl]methyl}(triphenyl)phosphanium bromideYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

74.2 g of triphenylphosphine (0.28 M) in 200 ml of acetonitrile are added to a solution of 74.5 g of methyl 2-bromomethylbenzoate (0.32 M) in 170 ml of acetonitrile in a 2000 ml reactor. The reaction mixture is refluxed with stirring for one hour and then cooled. 1000 ml of diethyl ether are then added slowly. Stirring is continued for 2 hours. A white precipitate forms. The solid is filtered off and washed with acetone. After drying, 112.6 g of a white powder are obtained (81% yield).

Workup

  1. temperatureThe reaction mixture is refluxed
  2. temperaturecooled
  3. stirringStirring
  4. waitis continued for 2 hours
  5. filtrationThe solid is filtered off
  6. washwashed with acetone
  7. customAfter drying

Sources & evidence

ORD record
ord-f1d5ec5a8cf14981840eaf709b5f45b5
Source dataset
uspto-grants-2010_10
Patent number
US07816397B2

Reaction notes

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