Phenyl phosphorus dichloride → HCID 178419337, compound

HRID 1012363Notes

Reaction equation

HRID 1012363 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].Br[C-:7]1C=CC=[CH:8]1.[C-:12]1([Br:17])[CH:16]=[CH:15][CH:14]=[CH:13]1.[Fe+2:18].[C:19]1([P:25]([Cl:27])Cl)[CH:24]=[CH:23][CH:22]=[CH:21]C=1.ClP>C1COCC1>[C:5]1([C-:21]2[CH:22]=[CH:23][CH:24]=[C:19]2[PH:25][Cl:27])[CH:8]=[CH:7][CH:2]=[CH:3][CH:4]=1.[Br:17][C-:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.[Fe+2:18]

Participants

6

Reactant 4

HCID 12573Phenyl phosphorus dichlorideHCID 161938Phosphorus chlorideHCID 15181852DibromoferroceneHCID 178418339Butyllithium

Product 1

HCID 178419337HCID 178419337, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

14.5 ml (23.2 mmol) of n-BuLi (1.6 M in hexane) are added dropwise to a solution of 8 g (23.2 mmol) of 1,1′-dibromoferrocene in 30 ml of THF at a temperature of <−30° C. The mixture is stirred for another 30 minutes at this temperature. It is then cooled to −78° C. and 3.15 ml (23.2 mmol) of phenyldichlorophosphine are added dropwise at such a rate that the temperature does not exceed −60° C. After stirring at −78° C. for a further 10 minutes, the temperature is allowed to rise to room temperature and the mixture is stirred for another one hour. This gives a suspension of the monochlorophosphine X1.

Workup

  1. customdoes not exceed −60° C
  2. stirringAfter stirring at −78° C. for a further 10 minutes
  3. customto rise to room temperature
  4. stirringthe mixture is stirred for another one hour
  5. customThis gives

Sources & evidence

ORD record
ord-353ed4df633c4d8fad630eaaf57aea05
Source dataset
uspto-grants-2011_07
Patent number
US07977499B2

Reaction notes

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