Triphenylphosphine → HCID 21757282, compound

HRID 274342Notes

Reaction equation

HRID 274342 reaction equation
[Br:1][CH:2]([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[Br-:1].[C:26]1([P+:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:2]([CH3:12])[C:3]([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=2)=[O:4])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 37882192-Bromo-1-(4-chlorophenyl)propan-1-one

Product 1

HCID 21757282HCID 21757282, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 2-bromo-4'-chloropropiophenone (58.1 g), which had been prepared in Example 5, and triphenyl phosphine (61.6 g) were dissolved in 250 ml of acetonitrile. The resulting solution was heated under reflex for 1.5 hours. After the completion of the reaction, the reaction mixture was cooled with ice, and the crystalline material thus formed was separated by filtration, washed with cold acetonitrile and dried in air to give triphenyl[1-(4-chlorophenyl)-1-oxo-2-propyl]-phosphonium bromide (79.0 g). mp 258°-258.5° C.

Workup

  1. temperatureThe resulting solution was heated under reflex for 1.5 hours
  2. customAfter the completion of the reaction
  3. temperaturethe reaction mixture was cooled with ice
  4. customthe crystalline material thus formed
  5. customwas separated by filtration
  6. washwashed with cold acetonitrile
  7. customdried in air

Sources & evidence

ORD record
ord-d7c14264f48347a98e470a37cc33cfd2
Source dataset
uspto-grants-1995_02
Patent number
US05389648

Reaction notes

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