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Dichloromethane → (3,3-difluorocyclobutyl)methyl methanesulfonate

HRID 1844173
Notes
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Reaction equation

HRID 1844173 reaction equation
[F:1][C:2]1([F:8])[CH2:5][CH:4]([CH2:6][OH:7])[CH2:3]1.ClCCl.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>O>[CH3:19][S:20]([O:7][CH2:6][CH:4]1[CH2:5][C:2]([F:8])([F:1])[CH2:3]1)(=[O:22])=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 45480377(3,3-Difluorocyclobutyl)methanol

Product 1

HCID 58223412(3,3-difluorocyclobutyl)methyl methanesulfonateYield 107%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

1.35 g (11.06 mmol) of (3,3-difluorocyclobutyl)methanol were initially charged in 41.8 ml of abs. dichloromethane, 3.08 ml (22.11 mmol) of triethylamine and 1.03 ml (13.27 mmol) of methanesulphonyl chloride were added and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture and the aqueous phase was extracted twice with dichloromethane. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and filtered, and the filtrate was concentrated. This gave 2.37 g (quantitative yield) of the target compound.

Workup

  1. extractionthe aqueous phase was extracted twice with dichloromethane
  2. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0415840638ca43a9a7ea8438ddec31b6
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946215B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes