2,2,2-Trifluoroethanol → HCID 59570318, compound

HRID 1880755Notes

Reaction equation

HRID 1880755 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].[Cl:9][C:10]1[C:11]([C:18]#[N:19])=[N:12][CH:13]=[C:14]([Cl:17])[C:15]=1Cl.[Cl-].[NH4+]>O1CCCC1>[Cl:9][C:10]1[C:11]([C:18]#[N:19])=[N:12][CH:13]=[C:14]([Cl:17])[C:15]=1[O:6][CH2:5][C:4]([F:8])([F:7])[F:3]

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 7286733,4,5-Trichloropyridine-2-carbonitrile

Product 1

HCID 59570318HCID 59570318, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into 5 ml of tetrahydrofuran was suspended 0.12 g of sodium hydride (60% oily), and 0.27 g of trifluoroethyl alcohol was added at 10° C. After stirring for 10 minutes, 0.5 g of 3,4,5-trichloropyridine-2-carbonitrile was added at 0° C., the mixture was stirred for 20 hours, and the reaction solution was poured into an aqueous saturated ammonium chloride solution, followed by extraction with tert-butyl=methyl=ether three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.6 g of 3,5-dichloro-4-(2,2,2-trifluoroethoxy)pyridine-2-carbonitrile. 3,5-Dichloro-4-(2,2,2-trifluoroethoxy)pyridine-2-carbonitrile

Workup

  1. additionwas added at 10° C
  2. stirringthe mixture was stirred for 20 hours
  3. extractionfollowed by extraction with tert-butyl=methyl=ether three times
  4. washwashed with an aqueous saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cd51dc61ed1049feae899bc08d8d5ec9
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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