Triphenylphosphine → HCID 86668455, compound

HRID 2039362Notes

Reaction equation

HRID 2039362 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][Br:13])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[Br-:13].[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][P+:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 57197627HCID 57197627, compound

Product 1

HCID 86668455HCID 86668455, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

3-(4-Propylphenyl)bromopropane (s4) (14.0 g), toluene (100 ml) and triphenylphosphine (31.5 g) were placed in a reaction vessel under an atmosphere of nitrogen, and the mixture was heated to reflux for 5 hours. After the reaction mixture had been cooled to 25° C., the deposits were filtered, and the unreacted material was removed by washing with toluene three times. The resulting colorless solids were dried to give 3-(4-propylphenyl)propyltriphenyl phosphonium bromide (s5) (30.0 g). The yield based on the compound (s4) was 99.1%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 hours
  3. filtrationthe deposits were filtered
  4. customthe unreacted material was removed
  5. washby washing with toluene three times
  6. customThe resulting colorless solids were dried

Sources & evidence

ORD record
ord-4c96a737c9d842c9a65608b399403740
Source dataset
uspto-grants-2013_11
Patent number
US08580146B2

Reaction notes

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