Triphenylphosphine → 6-[3-(Aminocarbonyl)phenoxy]hexyl(triphenyl)phosphonium bromide

HRID 415569Notes

Reaction equation

HRID 415569 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([C:15]([NH2:17])=[O:16])[CH:12]=[CH:13][CH:14]=1.[C:18]1([P:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC#N>[Br-:1].[NH2:17][C:15]([C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][P+:24]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:16]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 594029303-[(6-Bromohexyl)oxy]benzenecarboxamide

Product 1

HCID 866432706-[3-(Aminocarbonyl)phenoxy]hexyl(triphenyl)phosphonium bromideYield 101.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-[(6-bromohexyl)oxy]benzenecarboxamide (2.10 g, 7 mmol, 1 equiv.) and triphenylphosphine (1.93 g, 7.35 mmol, 1.05 equiv.) in CH3CN (30 ml) was heated under reflux for 72 h. The solvent was evaporated under reduced pressure and the residue was triturated with dry Et2O until it solidified. The solid was filtered and dried in vacuo to give the desired compound as a white solid (4.0 g, 100%). HPLC-MS (method 1): m/z 482 [M−Br]+, Rt=3.65 min.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 72 h
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was triturated with dry Et2O until it
  5. filtrationThe solid was filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-153171d2e9b2453ebbfa5b12aca05844
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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