Dichloromethane → 1132843-09-4

HRID 1624115Notes

Reaction equation

HRID 1624115 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]

Participants

6

Reactant 4

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

Product 1

HCID 582234121132843-09-4Yield 107%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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-9db73f28bfd2496ba17de57e3ead988d
Source dataset
uspto-grants-2014_07
Patent number
US08778964B2

Reaction notes

Loading…