4-Toluenesulfonyl chloride → (4,4-Difluorocyclohexyl)methyl 4-methylbenzenesulfonate

HRID 1443602Notes

Reaction equation

HRID 1443602 reaction equation
[F:1][C:2]1([F:10])[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH2:3]1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1>[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17]([O:9][CH2:8][CH:5]2[CH2:6][CH2:7][C:2]([F:10])([F:1])[CH2:3][CH2:4]2)(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 21184133(4,4-Difluorocyclohexyl)methanol

Product 1

HCID 23224632(4,4-Difluorocyclohexyl)methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The above (4,4-difluorocyclohexyl)methanol was dissolved in 5 ml of pyridine. Thereto 2.2 g of p-toluenesulfonyl chloride was added at 0° C. and the mixture was stirred at room temperature overnight. Thereafter, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed successively with water, dilute hydrochloric acid and aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 3.1 g of 4,4-difluorocyclohexylmethyl p-toluenesulfonate.

Workup

  1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed successively with water, dilute hydrochloric acid and aqueous saturated sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-17d1a2b54d9e4f22a0c448a50dbe646c
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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