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Water → [4-(Benzenesulfonyl)phenyl]phenylphosphinic acid

HRID 2082787
Notes
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Reaction equation

HRID 2082787 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13](N)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:17][B-:18]([F:21])([F:20])[F:19].[C:22]1([S:28]([C:31]2[CH:36]=[CH:35][C:34]([N+:37]#[N:38])=[CH:33][CH:32]=2)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl[P:40](Cl)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(OCC)(=[O:50])C.[OH2:54]>[Cu]Cl>[F:17][B-:18]([F:21])([F:20])[F:19].[C:22]1([S:28]([C:31]2[CH:36]=[CH:35][C:34]([N+:37]#[N:38])=[CH:33][CH:32]=2)(=[O:29])=[O:30])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1.[C:41]1([P:40]([C:13]2[CH:14]=[CH:15][C:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])=[CH:11][CH:12]=2)(=[O:50])[OH:54])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 12573Phenyl phosphorus dichlorideHCID 5166664-(Phenylsulfonyl)anilineHCID 20360589HCID 20360589, compound

Product 2

HCID 20360589HCID 20360589, compound
HCID 20360606
[4-(Benzenesulfonyl)phenyl]phenylphosphinic acid
Yield 45%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

4-(phenylsulfonyl)benzene diazonium tetrafluoroborate was prepared from 4-aminophenyl phenyl sulfone according to the method of example 11. A slurry of 44 grams of the 4-(phenylsulfonyl)benzenediazonium tetrafluoroborate, 22.8 ml of dichlorophenylphosphine, and 0.5 grams of copper (I) chloride in 400 ml. of ethyl acetate was heated at 30° C for 1.5 hours, cooled, and decomposed by adding 125 ml. of water. The ethyl acetate was removed by steam distillation, and the solid was collected by filtration of the aqueous residue. This solid was extracted with 2 liter of 10% sodium hydroxide, and the extract was acidified with hydrochloric acid to give crude acid. Crystallization from 80% ethanol gave 20 grams (45% yield) of phenyl[4-(phenylsulfonyl)phenyl]phosphinic acid, m.p. 225°-228° C.

Workup

  1. temperaturecooled
  2. additionby adding 125 ml
  3. customThe ethyl acetate was removed by steam distillation
  4. filtrationthe solid was collected by filtration of the aqueous residue
  5. extractionThis solid was extracted with 2 liter of 10% sodium hydroxide
  6. customto give crude acid
  7. customCrystallization from 80% ethanol

Sources & evidence

ORD record
ord-13e49f5e1df549e1962054d1a7a06e81
Source dataset
uspto-grants-1978_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04082793

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes