Triphenylphosphine → HCID 86730714, compound

HRID 633841Notes

Reaction equation

HRID 633841 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][CH2:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][C:24]=1[Cl:35]>CC1C=CC(C)=CC=1>[Br-:20].[Cl:35][C:24]1[CH:25]=[N:26][C:27]2[C:32]([C:23]=1[CH2:22][CH2:21][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86730716HCID 86730716, compound

Product 1

HCID 86730714HCID 86730714, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

Triphenylphosphine (27.7 g, 106.0 mmol, 3.0 eq) is added at room temperature to a stirred solution of 4-(2-bromo-ethyl)-3-chloro-6-methoxy-quinoline (10.6 g, 35.3 mmol, 1.0 eq) in p-xylene (200 mL) and the reaction mixture is heated under reflux for 20 hours. The resulting precipitate is collected by filtration and washed with ethyl acetate (50 mL) to afford [2-(3-chloro-6-methoxy-quinolin-4-yl)-ethyl]-triphenyl-phosphonium bromide as a light yellow solid (18.2 g, 92% yield).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 20 hours
  3. filtrationThe resulting precipitate is collected by filtration
  4. washwashed with ethyl acetate (50 mL)

Sources & evidence

ORD record
ord-18e589fe5e10447099fec3c3b85e0249
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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