Triphenylphosphine → 3-(4-Ethoxy-2,3-difluorophenyl)propyltriphenylphosphonium bromide

HRID 2039369Notes

Reaction equation

HRID 2039369 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][Br:13])=[C:6]([F:14])[C:5]=1[F:15])[CH3:2].[C:16]1([P:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[Br-:13].[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][P+:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:6]([F:14])[C:5]=1[F:15])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 22913643HCID 22913643, compound

Product 1

HCID 866684593-(4-Ethoxy-2,3-difluorophenyl)propyltriphenylphosphonium bromideYield 78.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

3-(4-Ethoxy-2,3-difluorophenyl)bromopropane (s22) (11.5 g), toluene (100 ml) and triphenylphosphine (21.6 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-ethoxy-2,3-difluorophenyl)propyltriphenylphosphonium bromide (s23) (17.6 g). The yield based on the compound (s22) was 78.9%.

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-614171ea941d4da4ba03a9bd037ad63c
Source dataset
uspto-grants-2013_11
Patent number
US08580146B2

Reaction notes

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