4-Nitrobenzenesulfonyl chloride → (2,2-Difluorocyclopropyl)methyl 4-nitrobenzenesulfonate

HRID 2277246Notes

Reaction equation

HRID 2277246 reaction equation
[F:1][C:2]1([F:7])[CH2:4][CH:3]1[CH2:5][OH:6].C(N(CC)CC)C.[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1)([O-:17])=[O:16].C(=O)([O-])O.[Na+]>C1COCC1>[N+:15]([C:18]1[CH:19]=[CH:20][C:21]([S:24]([O:6][CH2:5][CH:3]2[CH2:4][C:2]2([F:7])[F:1])(=[O:26])=[O:25])=[CH:22][CH:23]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2761401(2,2-Difluorocyclopropyl)methanol

Product 1

HCID 86731319(2,2-Difluorocyclopropyl)methyl 4-nitrobenzenesulfonateYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2,2-difluorocyclopropyl)methanol (20.0 g) and triethylamine (32.2 mL) in THF (300 mL) was added 4-nitrobenzenesulfonyl chloride (41.0 g) at 0° C., and the mixture was stirred for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (47.2 g) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4c9643ebc5074a0989c13ac531fd70bc
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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