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

HRID 1686853Notes

Reaction equation

HRID 1686853 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

10.4 g (0.060 mol) of 3-bromophenol, 17.3 g (0.066 mol) of triphenyl phosphine, 0.65 g (5 mmol) of nickel chloride, and 40 ml of ethylene glycol were put into a separable flask (volume, 200 ml) equipped with a condenser and a stirrer, and reacted with stirring under heat at 160° C. The reaction liquid was cooled, 40 ml of pure water was dropwise added thereto, and the deposited crystal was washed with toluene, taken out through filtration, and dried to obtain triphenyl(3-hydroxyphenyl)phosphonium bromide.

Workup

  1. custom(volume, 200 ml) equipped with a condenser and a stirrer
  2. customreacted
  3. customThe reaction liquid
  4. temperaturewas cooled
  5. washthe deposited crystal was washed with toluene
  6. filtrationtaken out through filtration
  7. customdried

Sources & evidence

ORD record
ord-447b28080c6b4046aef4068d7c2cd559
Source dataset
uspto-grants-2012_04
Patent number
US08148831B2

Reaction notes

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