Triphenyl phosphite → HCID 89783263, compound

HRID 2173704Notes

Reaction equation

[F:1][C:2]([P:8]([C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])(=[O:11])[O:9]C)([F:7])[C:3]([F:6])([F:5])[F:4].[P:19]([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[F:7][C:2]([P:8]([C:12]([F:17])([F:18])[C:13]([F:16])([F:15])[F:14])(=[O:9])[O-:11])([F:1])[C:3]([F:6])([F:5])[F:4].[CH3:2][P+:19]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[O:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Reactant 2

HCID 7540Triphenyl phosphite2×

HCID 23081881HCID 23081881, compound4×

Product 1

HCID 89783263HCID 89783263, compoundYield 91%

Conditions

Temperature: 60 °C

Procedure

Methyl bis(pentafluoroethyl)phosphinate, (C2F5)2P(O)OCH3, (2.755 g; 8.7 mmol) is added at room temperature to triphenyl phosphite, P(OC6H5)3, (2.075 g; 6.7 mmol) in a 10 ml glass flask. The two-phase reaction mixture is warmed and stirred at 60° C. for 5.5 h. A cloudy and colourless reaction mixture forms, that is stirred at RT for 16 h and at 60° C. for 5 h. Methyl bis(pentafluoroethyl)phosphinate, (C2F5)2P(O)OCH3, (0.380 g; 1.2 mmol) is added again, and the mixture is again stirred at 60° C. for 5.5 h. Methyltriphenoxyphosphonium bis(pentafluoroethyl)phosphinate, [(C6H5O)3PCH3]-[(C2F5)2P(O)O], can be isolated as white and crystalline solid (3.827 g; 6.1 mmol) in a yield of 91% and a purity of 89% by purification in vacuo (10−3 mbar) at 80° C.

Workup

customThe two-phase reaction mixture
temperatureis warmed
stirringA cloudy and colourless reaction mixture forms, that is stirred at RT for 16 h and at 60° C. for 5 h
stirringthe mixture is again stirred at 60° C. for 5.5 h

Sources & evidence

ORD record: ord-d3b009e2376d4ef1a898bc287d429475
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056881B2

Reaction notes

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