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Ethylene Glycol → (2-Hydroxyphenyl)tris(4-methoxyphenyl)phosphanium bromide

HRID 1686854
Notes
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Reaction equation

HRID 1686854 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([P:17]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1.C(O)CO>[Ni](Cl)Cl.O>[Br-:1].[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([P+:17]([C:26]2[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[OH:8])=[CH:19][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 72442-BromophenolHCID 70071Phosphine, tris(4-methoxyphenyl)-

Product 1

HCID 71403132(2-Hydroxyphenyl)tris(4-methoxyphenyl)phosphanium bromide

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalyst
HCID 962
Water
Solvent

Conditions

Temperature
160 °C

Procedure

10.4 g (0.060 mol) of 2-bromophenol, 23.20 g (0.066 mol) of tris(4-methoxyphenyl) 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 tris(4-methoxyphenyl)(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-a028361eb6cd40cd9192dc7287c710cd
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08148831B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes