Methanol → Methyl (4-cyano-2-fluoro-5-methoxyphenyl)acetate

HRID 1186984Notes

Reaction equation

HRID 1186984 reaction equation
[C:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH2:11][C:12]([OH:14])=[O:13])=[C:5]([F:15])[CH:4]=1)#[N:2].S(Cl)(Cl)=O.[CH3:20]O>>[CH3:20][O:13][C:12](=[O:14])[CH2:11][C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([C:1]#[N:2])=[CH:4][C:5]=1[F:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 665248932-(4-Cyano-2-fluoro-5-methoxyphenyl)acetic acid

Product 1

HCID 86694457Methyl (4-cyano-2-fluoro-5-methoxyphenyl)acetate

Procedure

To a solution of (4-cyano-2-fluoro-5-methoxyphenyl)acetic acid (5.0 g, 24 mmol) in methanol (50 mL) at 0° C. was added thionyl chloride (2.3 mL, 31 mmol) drop-wise. The mixture warmed slowly to rt and stirred 12 h, then was concentrated in vacuo and dried under high vacuum to provide methyl(4-Cyano-2-fluoro-5-methoxyphenyl)acetate. 1H NMR (500 MHz, CD3OD) δ 7.35 (d, J=5.3 Hz, 1H), 7.19 (d, J=5.4 Hz, 1H), 3.96 (s, 3H), 3.82 (s, 3H), 3.81 (s, 2H).

Workup

  1. concentrationwas concentrated in vacuo
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-dcfedd2af0a74bedb67b59a69104c7b1
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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