Triphenylphosphine → (Carbethoxyhexyl)triphenylphosphonium bromide

HRID 523897Notes

Reaction equation

HRID 523897 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-8f7befaf863d499f89087fc2b7e08290
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Reaction notes

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