Phenylphosphorus tetrachloride → Bis(nonafluorobutyl)phosphinyl chloride

HRID 389398Notes

Reaction equation

HRID 389398 reaction equation
[F:1][C:2]([F:29])([C:25]([F:28])([F:27])[F:26])[C:3]([F:24])([F:23])[C:4]([P:7]([C:10]([F:22])([F:21])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])(=O)[OH:8])([F:6])[F:5].C1(P(Cl)(Cl)(Cl)[Cl:37])C=CC=CC=1>C(Cl)(Cl)Cl>[F:1][C:2]([F:29])([C:25]([F:28])([F:27])[F:26])[C:3]([F:24])([F:23])[C:4]([P:7]([Cl:37])([C:10]([F:22])([F:21])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])=[O:8])([F:6])[F:5]

Participants

4

Reactant 2

HCID 12468899Phenylphosphorus tetrachlorideHCID 14169491Bis(nonafluorobutyl)phosphinic acid

Product 1

HCID 14294507Bis(nonafluorobutyl)phosphinyl chlorideYield 63%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Variant a) 2.49 g (5.0 mmol) of bis(nonafluorobutyl)phosphinic acid are added dropwise at room temperature to a solution of 1.47 g (5.9 mmol) of phenyltetrachlorophosphorane in 3 cm3 of dry chloroform, and the mixture is stirred for a further 50 minutes. Chloroform is separated off by distillation, and bis(nonafluorobutyl)phosphinyl chloride is distilled off at atmospheric pressure, giving 1.62 g of bis(nonafluorobutyl)phosphinyl chloride, which corresponds to a yield of 63%, based on the phosphinic acid employed.

Workup

  1. customChloroform is separated off by distillation, and bis(nonafluorobutyl)phosphinyl chloride
  2. distillationis distilled off at atmospheric pressure

Sources & evidence

ORD record
ord-88d9895385414e8f965a01520f846748
Source dataset
uspto-grants-2013_02
Patent number
US08378157B2

Reaction notes

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