Ethylene Glycol → 2-Hydroxyphenyltriphenylphosphonium bromide

HRID 1686852Notes

Reaction equation

HRID 1686852 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[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]=[CH:4][C:3]=2[OH:8])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 72442-BromophenolHCID 11776Triphenylphosphine

Product 1

HCID 573460052-Hydroxyphenyltriphenylphosphonium bromide

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

10.4 g (0.060 mol) of 2-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(2-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-fdb418a511e3424880f528e648deee8c
Source dataset
uspto-grants-2012_04
Patent number
US08148831B2

Reaction notes

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