Methanesulfonyl chloride → (R)-1-(5-fluoro-2-methylphenyl)propan-2-yl methanesulfonate

HRID 920464Notes

Reaction equation

HRID 920464 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH2:8][C@H:9]([OH:11])[CH3:10])[CH:7]=1.CCN(C(C)C)C(C)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:22][S:23]([O:11][C@H:9]([CH3:10])[CH2:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[CH3:12])(=[O:25])=[O:24]

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 66687280(2R)-1-(5-fluoro-2-methylphenyl)propan-2-ol

Product 1

HCID 86663209(R)-1-(5-fluoro-2-methylphenyl)propan-2-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-1-(5-fluoro-2-methylphenyl)propan-2-ol (6.1 g, 36.3 mmol) and DIEA (12.6 mL, 72.6 mmol) in 200 mL anhydrous DCM was cooled in ice-water bath. Then methylsulfonyl chloride (3.4 mL, 43.5 mmol) was added slowly and the mixture was stirred for 30 min at rt. And then, saturated NaHCO3 solution (30 mL) was added to the solution and extracted with DCM, dried over anhydrous MgSO4, concentrated, passed through silicagel pad to give crude (R)-1-(5-fluoro-2-methylphenyl)propan-2-yl methanesulfonate (F-2).

Workup

  1. extractionextracted with DCM
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e8f60eceb2834adfab7c53d07a378c94
Source dataset
uspto-grants-2016_03
Patent number
US09273055B2

Reaction notes

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