Triphenylphosphine → (Carbethoxyhexyl)triphenylphosphonium bromide

HRID 404141Notes

Reaction equation

HRID 404141 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][Br:11])[CH3:2].[CH:13]1[CH:18]=[CH:17][C:16]([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:15][CH:14]=1>C(#N)C>[Br-:11].[CH2:1]([O:3][C:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:16]1[CH:15]=[CH:14][CH:13]=[CH:18][CH:17]=1)=[O:12])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 122490Ethyl 7-bromoheptanoate

Product 1

HCID 10994694(Carbethoxyhexyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl-7-bromoheptanoate (2.5 g, 10.54 mmol) and PPh3 (2.764 g, 10.54 mmol) were added to acetonitrile (50 mL) and the mixture was stirred under Ar(g) at reflux for 18 h. The solvent was subsequently removed by evaporation under reduced pressure, and the resulting phosphonium bromide derivative I was dried under high vacuum.

Workup

  1. temperatureat reflux for 18 h
  2. customThe solvent was subsequently removed by evaporation under reduced pressure
  3. dry with materialthe resulting phosphonium bromide derivative I was dried under high vacuum

Sources & evidence

ORD record
ord-370f414784bb43da805a22f04261915a
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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