Hydrochloric Acid → Diphenylphosphine

HRID 2287765Notes

Reaction equation

HRID 2287765 reaction equation
BrCCBr.Cl[Si](C)(C)C.Cl[P:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>O1CCCC1.[Zn].C1(C)C=CC=CC=1>[C:18]1([PH:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 66180Chlorodiphenylphosphine

Product 1

HCID 70017DiphenylphosphineYield 84%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

20×10-3 cm3 of 1,2-dibromoethane was added dropwise in a nitrogen gas atmosphere to a suspension of 461 mg (7.05 mg-atoms) of zinc (powder) in 10 cm3 of tetrahydrofuran, the mixture was heated to reflux for about 2 minutes and cooled to room temperature, 30×10-3 cm3 of chlorotrimethylsilane was added and the mixture was stirred for about 2 minutes to prepare an activated zinc. Subsequently, 1.04 g (4.71 mmol) of chlorodiphenylphosphine was added dropwise and the mixture was stirred at room temperature. To the reaction mixture was added dropwise 10 cm3 (10 mmol) of 1 mol·dm-3 hydrochloric acid and then 10 cm3 of toluene. The mixture was stirred, the aqueous layer and the toluene layer were separated off, the toluene layer was determined by gas chromatography, giving diphenylphosphine in 84% yield.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for about 2 minutes
  3. stirringthe mixture was stirred at room temperature
  4. stirringThe mixture was stirred
  5. customthe aqueous layer and the toluene layer were separated off

Sources & evidence

ORD record
ord-19baea9353ec4018bdad5c8241c929f0
Source dataset
uspto-grants-2000_07
Patent number
US06084133

Reaction notes

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