2-(3-Cyano-4-fluorophenyl)acetic acid → Methyl 2-(3-cyano-4-fluorophenyl)acetate
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].Cl.[CH3:15]O>CO>[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][CH3:15])=[O:12])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of crude (3-cyano-4-fluorophenyl)acetic acid (980 mg, 5.6 mmol) in methanol (10 mL) was added 5 M HCl/MeOH (10 mL). The reaction was stirred at ambient temperature overnight and concentrated. The residue was purified with preparative TLC to afford methyl (3-cyano-4-fluorophenyl)acetate. 1H-NMR (300 MHz, CDCl3) δ ppm 7.49˜7.55 (m, 2H), 7.17 (t, J=8.2 Hz, 1H), 3.71 (s, 3H), 3.63 (s, 2H).
Workup
- concentrationconcentrated
- customThe residue was purified with preparative TLC
Sources & evidence
- ORD record
- ord-5ce911aad0414090aaee5885cf14fa25
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09056859B2
Reaction notes
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