4-(2,3-Dihydroxypropyl)-2-fluorobenzonitrile → 2-Fluoro-4-(2-oxoethyl)benzonitrile
Reaction equation
[OH:1][CH:2](CO)[CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([F:12])[CH:5]=1>CO.O>[F:12][C:6]1[CH:5]=[C:4]([CH2:3][CH:2]=[O:1])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of 4-(2,3-dihydroxypropyl)-2-fluorobenzonitrile (500 mg, 2.6 mmol) in 10 mL of methanol and 3 mL of water was cooled to 0° C. by ice bath, then NaIO4 (820 mg, 3.8 mmol) was added and the mixture was stirred at 0° C. for two hours. The reaction was monitored according to TLC. The mixture was filtered and concentrated. The residue was dissolved in DCM, dried over anhydrous sodium sulfate, and then purified by flash column chromatography to give 2-fluoro-4-(2-oxoethyl)benzonitrile. MS m/z: 164 (M+1)+.
Workup
- filtrationThe mixture was filtered
- concentrationconcentrated
- dissolutionThe residue was dissolved in DCM
- dry with materialdried over anhydrous sodium sulfate
- custompurified by flash column chromatography
Sources & evidence
- ORD record
- ord-e6da56c1e0494bd09f771de800ef92c3
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073882B2
Reaction notes
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