Potassium Hydroxide → 2-(3-Fluoro-4-(methylthio)phenyl)acetic acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10](=O)[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].O.NN.[OH-].[K+].C(OCC)(=O)C.CCCCCC>C(OCC)(=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
2-(3-Fluoro-4-(methylthio)phenyl)-2-oxoacetic acid (4.5 g, crude) was added to hydrazine hydrate (5.1 mL, 5 eq) at −50° C. The contents were heated to 80° C., KOH (2.7 g, 2.3 eq) was added and the overall reaction mixture was stirred for 12 h at 100° C. Progress of the reaction was monitored by TLC (50% ethyl acetate/hexane, Rf˜0.8). On completion of the reaction, to the contents was added water and ethyl acetate and the layers were separated. The aqueous layer was acidified with diluted HCl at 0-5° C., the precipitate was filtered and dried to yield 2-(3-fluoro-4-(methylthio)phenyl)acetic acid as a white colored solid (3 g, 71%).
Workup
- customOn completion of the reaction
- customthe layers were separated
- customwas acidified with diluted HCl at 0-5° C.
- filtrationthe precipitate was filtered
- customdried
Sources & evidence
- ORD record
- ord-0d94118694a14174b7294aae26979d96
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946204B2
Reaction notes
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