2-(3-Cyano-4-fluorophenyl)acetic acid → Methyl 2-(3-cyano-4-fluorophenyl)acetate

HRID 2173229Notes

Reaction equation

HRID 2173229 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

HCID 27739352-(3-Cyano-4-fluorophenyl)acetic acidHCID 21893726Hydrochloride methanol

Product 1

HCID 68513176Methyl 2-(3-cyano-4-fluorophenyl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. concentrationconcentrated
  2. customThe residue was purified with preparative TLC

Sources & evidence

ORD record
ord-5ce911aad0414090aaee5885cf14fa25
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…