Triphenylphosphine → HCID 86650873, compound

HRID 2061563Notes

Reaction equation

HRID 2061563 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][C:4]=1[NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14].[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>C1(C)C=CC=CC=1>[Br-:1].[C:9]([C:7]1[CH:6]=[CH:5][C:4]([NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])=[C:3]([CH2:2][P+:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:8]=1)#[N:10]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 58138932HCID 58138932, compound2×

Product 1

HCID 86650873HCID 86650873, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

In a 250 mL round-bottomed flask N-[2-(bromomethyl)-4-cyanophenyl]-2,2,2-trifluoroacetamide (Intermediate 6, 6 g, 19.54 mmol) was dissolved in toluene (100 mL). Triphenylphosphine (5.12 g, 19.54 mmol) was added and the reaction mixture heated to 85° C. under argon for 5 hrs. The reaction mixture was allowed to cool to room temperature and the resulting yellow solid was collected, washed well with toluene, to give the title compound as a yellow solid (6.5 g);

Workup

  1. temperatureto cool to room temperature
  2. customthe resulting yellow solid was collected
  3. washwashed well with toluene

Sources & evidence

ORD record
ord-481c6abff793423aabd105f48fb99c98
Source dataset
uspto-grants-2012_10
Patent number
US08283365B2

Reaction notes

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