Ethylene Glycol → (3-Hydroxyphenyl)(triphenyl)phosphanium bromide

HRID 2241061Notes

Reaction equation

HRID 2241061 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]1([P:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)CO>[Ni](Cl)Cl.O>[Br-:1].[C:22]1([P+:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 115633-BromophenolHCID 11776Triphenylphosphine

Product 1

HCID 71414619(3-Hydroxyphenyl)(triphenyl)phosphanium bromide

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

Into a separable flask (the capacity: 200 ml) equipped with a condenser and a stirrer, 10.4 g (0.060 moles) of 3-bromophenol, 17.3 g (0.066 moles) of triphenylphosphine, 0.65 g (5 mmole) of nickel chloride and 40 ml of ethylene glycol were placed, and the reaction was allowed to proceed by heating at 160° C. under stirring. After the reaction solution was cooled, 40 ml of pure water was slowly added dropwise. The separated crystals were washed with toluene, separated by filtration and dried, and triphenyl(3-hydroxyphenyl)phosphonium bromide was obtained

Workup

  1. customInto a separable flask (the capacity: 200 ml) equipped with a condenser and a stirrer
  2. temperatureAfter the reaction solution was cooled
  3. washThe separated crystals were washed with toluene
  4. customseparated by filtration
  5. customdried

Sources & evidence

ORD record
ord-1e24cf1567c74598ac1efd120984f1fc
Source dataset
uspto-grants-2010_05
Patent number
US07723444B2

Reaction notes

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