Phenol → (2-Phenoxyethyl)triphenylphosphonium bromide

HRID 962458Notes

Reaction equation

HRID 962458 reaction equation
[C:1]1([O:7][CH2:8][CH2:9][Br:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(O)C=CC=CC=1>CCOCC>[Br-:10].[O:7]([CH2:8][CH2:9][P+:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11776TriphenylphosphineHCID 68526Benzene, (2-bromoethoxy)-

Product 1

HCID 2778279(2-Phenoxyethyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-bromoethyl phenyl ether (20.0 g), triphenylphosphine (26.2 g) and phenol (200 g) was heated at 90° C. with stirring for 48 hours. The mixture was cooled to approximately 40° C. and added to ether (1500 ml). The ether was decanted off and the residual oil was triturated with ether until a solid was obtained. The solid was collected by filtration to give (2-phenoxyethyl)triphenylphosphonium bromide.

Workup

  1. temperatureThe mixture was cooled to approximately 40° C.
  2. customThe ether was decanted off
  3. customthe residual oil was triturated with ether until a solid
  4. customwas obtained
  5. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-bbf20ffc748c470885f435bb69b08a7d
Source dataset
uspto-grants-1998_06
Patent number
US05760035

Reaction notes

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