Triphenylphosphine → HCID 20063318, compound

HRID 1084452Notes

Reaction equation

HRID 1084452 reaction equation
[Br:1][CH2:2][C:3]1[N:4]([CH:21]([CH3:23])[CH3:22])[C:5](=[O:20])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[C:24]1([P:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[Br-:1].[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:20])[N:4]([CH:21]([CH3:23])[CH3:22])[C:3]=2[CH2:2][P+:30]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 200633113-Bromomethyl-4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinoline

Product 1

HCID 20063318HCID 20063318, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-bromomethyl-4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinoline (5.8 g) in toluene (120 ml) was treated with triphenylphosphine (4.1 g), and the resulting mixture was stirred and heated at reflux for 1 hour, during which time a white crystalline solid precipitated from the solution. The solid was filtered off, and washed with petroleum ether (b.p. 60°-80° C.), to give [4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl]methyltriphenylphosphonium bromide, in the form of a white crystalline solid (9.64 g), m.p. 274° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour, during which time a white crystalline solid
  3. customprecipitated from the solution
  4. filtrationThe solid was filtered off
  5. washwashed with petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-12ede43488a1453cad8a549ba6237946
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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