Pyridine → 5-(3-(3,5-Dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-fluorobenzonitrile

HRID 1848309Notes

Reaction equation

HRID 1848309 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](O)([C:22]([F:25])([F:24])[F:23])[CH2:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]([F:21])=[C:17]([CH:20]=2)[C:18]#[N:19])=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.S(Cl)(Cl)=O.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:22]([F:25])([F:24])[F:23])=[CH:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]([F:21])=[C:17]([CH:20]=2)[C:18]#[N:19])=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 866421905-(3-(3,5-Dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)-2-fluorobenzonitrile

Product 1

HCID 866421895-(3-(3,5-Dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-fluorobenzonitrileYield 85.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After adding 5.85 g of toluene to 1.95 g (4.81 mmol) of 5-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)-2-fluorobenzonitrile, 1.14 g (9.62 mmol) of thionyl chloride and 0.76 g (9.62 mmol) of pyridine were added at 80° C., and stirred for 2 hours. The reaction solution was cooled to room temperature, and separated by adding 20 ml of toluene and 10 ml of water. After washing the toluene phase with an aqueous solution of 0.39 g of sodium hydroxide dissolved into 10 ml of water, the phase was washed with water. The solvent was distilled off under reduced pressure to obtain 1.59 g of 5-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-fluorobenzonitrile (yield 85.2%).

Workup

  1. additionwere added at 80° C.
  2. customseparated
  3. additionby adding 20 ml of toluene and 10 ml of water
  4. washAfter washing the toluene phase with an aqueous solution of 0.39 g of sodium hydroxide
  5. dissolutiondissolved into 10 ml of water
  6. washthe phase was washed with water
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-17ce7b9b98044bc0b36aa2cac5096454
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

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