Methanol → 4-(2,3-Dihydroxypropyl)-2,6-difluorobenzonitrile

HRID 1519588Notes

Reaction equation

HRID 1519588 reaction equation
[CH2:1]([C:4]1[CH:11]=[C:10]([F:12])[C:7]([C:8]#[N:9])=[C:6]([F:13])[CH:5]=1)C=C.C[N+]1([O-])CC[O:18][CH2:17]C1.[CH3:22][OH:23]>O.O=[Os](=O)(=O)=O>[OH:23][CH:22]([CH2:17][OH:18])[CH2:1][C:4]1[CH:11]=[C:10]([F:12])[C:7]([C:8]#[N:9])=[C:6]([F:13])[CH:5]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 82029Methyl morpholine oxideHCID 675131164-Allyl-2,6-difluorobenzonitrile

Product 1

HCID 675141074-(2,3-Dihydroxypropyl)-2,6-difluorobenzonitrile

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a solution of 4-allyl-2,6-difluorobenzonitrile (1.7 g, 9.2 mmol) in 30 mL of methanol and 10 mL of water was added OsO4 (210 mg) and NMO (3.11 g, 23 mmol), and the mixture was stirred at ambient temperature overnight. Remove the methanol under reduced pressure, the residue was dissolved in EtOAc, washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by fast column chromatograph to give 4-(2,3-dihydroxypropyl)-2,6-difluorobenzonitrile. MS m/z: 214 (M+1)+.

Workup

  1. customRemove the methanol under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by fast column chromatograph

Sources & evidence

ORD record
ord-c29700cfe1e244579bba32b714877f48
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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