Hydrochloric Acid → 2-(3-Fluoro-4-(methylthio)phenyl)-2-oxoacetic acid

HRID 1843002Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:10](=[O:16])[C:11]([O:13]CC)=[O:12])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].C(OCC)(=O)C.CCCCCC.Cl>C1(C)C=CC=CC=1.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]([C:10](=[O:16])[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 2-(3-fluoro-4-(methylthio)phenyl)-2-oxoacetate (5.5 g, 0.02 mol) in toluene (55 mL, 10 times), 3 M sodium hydroxide solution (9.09 mL) was added at 50° C. and the reaction mixture was stirred for 3 h at the same temperature. Progress of the reaction was monitored by TLC (30% ethyl acetate/hexane, Rf˜0.1). On completion of the reaction, the contents were cooled to 0° C., the mixture was acidified with diluted HCl and the solid precipitated was filtered. The crude product 2-(3-fluoro-4-(methylthio)phenyl)-2-oxoacetic acid obtained as an yellow colored solid (4.5 g, crude) was directly used for the next step.

Workup

customOn completion of the reaction
customthe solid precipitated
filtrationwas filtered

Sources & evidence

ORD record: ord-b4138b506b0f4da494ef56de73793ff4
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946204B2

Reaction notes

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