Hydrochloric Acid → 4-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoic acid
Reaction equation
[OH-:1].[Na+].[CH2:3]([C:5]1[C:20]([F:21])=[CH:19][C:8]([O:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#N)=[CH:12][C:11]=2[F:18])=[C:7]([O:22][CH3:23])[CH:6]=1)[CH3:4].Cl.C(OCC)(=O)C.C[OH:32]>>[CH2:3]([C:5]1[C:20]([F:21])=[CH:19][C:8]([O:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]([OH:32])=[O:1])=[CH:12][C:11]=2[F:18])=[C:7]([O:22][CH3:23])[CH:6]=1)[CH3:4]Participants
Conditions
- Temperature
- 80 °C
Procedure
An aqueous solution of NaOH 6N (70 mL, 420 mmol) was added to a solution of 4-(4-ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzonitrile (which may be prepared in accordance with the experimental described in Example 4, step 3; 4.0 g, 13.82 mmol) in methanol (140 mL). The reaction mixture was then stirred at reflux (80° C.) overnight. After cooling to 0° C., the reaction mixture was acidified by slow addition of concentrated HCl (25 mL) until pH=2. The mixture was then diluted by addition of ethyl acetate (300 mL) and the aqueous layer was separated and extracted with ethyl acetate (2×200 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated under vacuum to afford the title product as a beige solid (4.20 g, quantitative).
Workup
- custommay be prepared in accordance with the
- temperatureAfter cooling to 0° C.
- customthe aqueous layer was separated
- extractionextracted with ethyl acetate (2×200 mL)
- dry with materialThe combined organic phases were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-601498c513574c8e92d8ee8aa8fc95e4
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383621B2
Reaction notes
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