2-Propanethiol → 2-Isopropylthio-3-fluoropyridine

HRID 1707235Notes

Reaction equation

HRID 1707235 reaction equation
[CH:1]([SH:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].F[C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][N:13]=1.C(OCC)(=O)C>CN(C)C=O>[CH:1]([S:4][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][N:13]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 63642-PropanethiolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27831762,3-Difluoropyridine

Product 1

HCID 199667562-Isopropylthio-3-fluoropyridineYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

181.2 g of isopropylmercaptan are added dropwise at a temperature of 0° to +2° C. in the course of 25 minutes to a suspension of 324 g of anhydrous potassium carbonate and 335.6 g of 2,3-difluoropyridine in 4500 ml of dimethylformamide. After the reaction mixture has been stirred for 18 hours at room temperature, it is poured into a mixture of 8000 ml of ice-water and 4000 ml of ethyl acetate. The organic phase is subsequently separated off and washed with ice-water and then with ethyl acetate. The combined organic phases are dried with sodium sulfate and subsequently concentrated. Purification by column chromatography over silica gel with ethyl acetate/n-hexane (1:9) gives 362.9 g of 2-isopropylthio-3-fluoropyridine in the form of an oil.

Workup

  1. customThe organic phase is subsequently separated off
  2. washwashed with ice-water
  3. dry with materialThe combined organic phases are dried with sodium sulfate
  4. concentrationsubsequently concentrated
  5. customPurification by column chromatography over silica gel with ethyl acetate/n-hexane (1:9)

Sources & evidence

ORD record
ord-7f53ab5dbbbd4e15be5ff1b11eefc683
Source dataset
uspto-grants-1994_10
Patent number
US05352654

Reaction notes

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