Isopropanol → 3-Chloro-2-(4-chloro-3-isopropoxycarbonylphenyl)-5-trifluoromethylpyridine

HRID 1957266Notes

Reaction equation

HRID 1957266 reaction equation
[Na].[Cl:2][C:3]1[C:4]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([C:20](OC)=[O:21])[CH:14]=2)=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH:24]([OH:27])([CH3:26])[CH3:25]>>[Cl:2][C:3]1[C:4]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([C:20]([O:27][CH:24]([CH3:26])[CH3:25])=[O:21])[CH:14]=2)=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 5360545SodiumHCID 19068738HCID 19068738, compound

Product 1

HCID 190687913-Chloro-2-(4-chloro-3-isopropoxycarbonylphenyl)-5-trifluoromethylpyridine

Conditions

Temperature
0 °C

Procedure

A small piece of sodium was added to a solution of 4.0 g of 3-chloro-2-(4-chloro-3-methoxycarbonylphenyl)-5-trifluoromethylpyridine in 20 ml of anhydrous isopropanol, followed by stirring at 0° C. for 20 hours. The solvent was then removed. The residue was taken up in 50 ml of water. The aqueous phase was extracted three times with 50 ml of tert-butyl methyl ether each time. The combined organic phases were dried over sodium sulfate and concentrated. Yield: 2.5 g (58%) of a colorless oil;

Workup

  1. customThe solvent was then removed
  2. extractionThe aqueous phase was extracted three times with 50 ml of tert-butyl methyl ether each time
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a6e9287d9549413aa10dc56f66f5ab6f
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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