(2-Amino-6-fluorophenyl)methanol → 2-Amino-6-fluorobenzaldehyde
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][OH:10]>ClCCl.O=[Mn]=O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]=[O:10]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To (2-amino-6-fluoro-phenyl)-methanol (2.49 g, 17.3 mmol) in dichloromethane (30 mL) was added MnO2 (3.01 g, 34.7 mmol, activated). The mixture was refluxed for 3 hrs and then filtered over celite. The mixture was concentrated and purified via silica gel flash chromatography (eluting with 30% ethyl acetate in hexane) to give 2-amino-6-fluoro-benzaldehyde as a yellow solid (1.23 g). tR=2.20 min. (method 1)
Workup
- temperatureThe mixture was refluxed for 3 hrs
- filtrationfiltered over celite
- concentrationThe mixture was concentrated
- custompurified via silica gel flash chromatography (eluting with 30% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-241e4afb3c544a729cff596a52563a5d
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422310B2
Reaction notes
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