Diethyl Ether → ((3-((7-Chloro-2-quinolinyl)methoxy)phenyl)methyl)triphenylphosphonium bromide

HRID 258467Notes

Reaction equation

HRID 258467 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[O:6][CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][C:12]([Cl:18])=[CH:13][CH:14]=2)[N:9]=1.[C:22]1([P:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCOCC>CC#N>[Br-:1].[Cl:18][C:12]1[CH:11]=[C:10]2[C:15]([CH:16]=[CH:17][C:8]([CH2:7][O:6][C:5]3[CH:4]=[C:3]([CH2:2][P+:28]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:21]=[CH:20][CH:19]=3)=[N:9]2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 197372372-((3-(Bromomethyl)phenoxy)methyl)-7-chloroquinoline

Product 1

HCID 88417068((3-((7-Chloro-2-quinolinyl)methoxy)phenyl)methyl)triphenylphosphonium bromideYield 98.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The bromide of Step 3 (26.45 g, 72.9 mmol) and triphenylphosphine (28.7 g, 109 mmol) were heated to reflux in CH3CN (250 mL) for 7 hours. At r.t., ether was added and an oil separated, which crystallized on trituration. The solid was filtered and was swished with ether for 20 hours to yield 44.87 g (98%) of the title phosphonium salt.

Workup

  1. customan oil separated
  2. customwhich crystallized on trituration
  3. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-714fb2a721da4fe497cb00166ba07611
Source dataset
uspto-grants-1993_11
Patent number
US05266568

Reaction notes

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