Pyridine → HCID 86642188, compound

HRID 1848306Notes

Reaction equation

HRID 1848306 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:24])[CH2:9][C:10]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)(O)[C:11]([F:14])([F:13])[F:12])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:24])[CH:9]=[C:10]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)[C:11]([F:12])([F:13])[F:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 86642185HCID 86642185, compound

Product 1

HCID 86642188HCID 86642188, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After adding 2.42 g of toluene to 0.81 g (1.82 mmol) of 1-(6-bromopyridin-3-yl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one, 0.44 g (3.64 mmol) of thionyl chloride and 0.29 g (3.64 mmol) of pyridine were added at 80° C., and stirred for 3 hours. The reaction solution was cooled to room temperature, and separated by adding 15 ml of ethyl acetate and 10 ml of water. After washing the ethyl acetate phase with an aqueous solution of 0.15 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 0.63 g of 1-(6-bromopyridin-3-yl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one (yield 81.4%).

Workup

  1. additionwere added at 80° C.
  2. customseparated
  3. additionby adding 15 ml of ethyl acetate and 10 ml of water
  4. washAfter washing the ethyl acetate phase with an aqueous solution of 0.15 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-1288d0e898a54c19b6e141fe32f6ef26
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

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