Pyridine → HCID 19860691, compound

HRID 868409Notes

Reaction equation

HRID 868409 reaction equation
[F:1][C:2]([F:8])([CH2:5][CH2:6][OH:7])[CH2:3][OH:4].N1C=CC=CC=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>ClCCl>[CH3:15][S:16]([O:4][CH2:3][C:2]([F:8])([F:1])[CH2:5][CH2:6][O:7][S:16]([CH3:15])(=[O:18])=[O:17])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 13935577108781-20-0

Product 1

HCID 19860691HCID 19860691, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 2,2-difluoro-1,4-butanediol (12.97 g, 103 mM), dry pyridine (65 mL) and dichloromethane (200 mL) is slowly added a solution of methanesulfonylchloride (23.6 g) in dichloromethane (50 mL). Stirring is continued overnight. The reaction mixture is washed with 2N HCl (twice), followed by 10% aqueous NaHCO3 until neutral, and then with water. The organic layer is dried (MgSO4) and upon evaporation of the solvents, a slightly yellow oil is obtained. Crystallization is induced by scratching the oil with dry ether, to yield the compound 1,4-bis-methanesulfonyloxy-2,2-difluorobutane as white crystals: 22.3 g (77%).

Workup

  1. washThe reaction mixture is washed with 2N HCl (twice),
  2. dry with materialThe organic layer is dried (MgSO4)
  3. customupon evaporation of the solvents
  4. customa slightly yellow oil is obtained
  5. customCrystallization

Sources & evidence

ORD record
ord-68accf6c674145728f9b0f11f3abd274
Source dataset
uspto-grants-1988_10
Patent number
US04778926

Reaction notes

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