Hydrochloric Acid → (4,4-Difluorocyclohexyl)methyl methanesulfonate

HRID 74426Notes

Reaction equation

HRID 74426 reaction equation
[F:1][C:2]1([F:10])[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH2:3]1.[CH3:11][S:12](Cl)(=[O:14])=[O:13].Cl>C(Cl)Cl>[CH3:11][S:12]([O:9][CH2:8][CH:5]1[CH2:6][CH2:7][C:2]([F:10])([F:1])[CH2:3][CH2:4]1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 21184133(4,4-Difluorocyclohexyl)methanol

Product 1

HCID 10868050(4,4-Difluorocyclohexyl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(4,4-Difluorocyclohexyl)methanol (0.7 g, 4.11 mmole) was stirred in CH2Cl2 (5 ml) and cooled in an ice bath. TEA (0.499 g, 4.93 mmoles) was added followed by methanesulfonyl chloride (0.518 g, 4.52 mmoles). Stirring was continued overnight while allowing to warm to room temp. 1.0 N HCl (30 ml) and CH2Cl2 (30 ml) was added and stirred for 5 min. The organic layer was dried over Na2SO4 and evaporated giving (4,4-difluorocyclohexyl)methyl methanesulfonate (142) as an oil. Yield (0.92 g, 98%): 1H NMR (400 MHz, DMSO-d6) δ 4.06 (d, J=6.4 Hz, 2H), 3.14 (s, 3H), 2.04-1.95 (m, 2H), 1.88-1.70 (m, 5H), 1.29-1.19 (m, 2H).

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirred for 5 min
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-290c3d43762d45db8c983d707c885b37
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

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