Ethanol → Ethyl 2-(5-amino-2-fluorophenyl)acetate
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1.S(=O)(=O)(O)O.C([O-])([O-])=O.[Na+].[Na+].[CH2:24](O)[CH3:25]>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([CH2:8][C:9]([O:11][CH2:24][CH3:25])=[O:10])[CH:7]=1Participants
5
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2-(5-amino-2-fluorophenyl)acetic acid (6.13 g, 36.2 mmol) in ethanol (15 mL) was added conc. sulfuric acid (2 mL) dropwise. The reaction mixture was stirred under N2 at 80° C. for 1 hr. After the reaction mixture was cooled to RT and neutralized with aqueous Na2CO3 to pH 7-8, the aqueous solution was extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with brine, dried over Na2SO4 and evaporated under vacuum to afford ethyl 2-(5-amino-2-fluorophenyl)acetate as a yellow oil which was used for the next step without further purification (6.13 g, 95%).
Workup
- extractionthe aqueous solution was extracted with ethyl acetate (3×100 mL)
- washThe combined organic layer was washed with brine
- dry with materialdried over Na2SO4
- customevaporated under vacuum
Sources & evidence
- ORD record
- ord-2aeaf586c4f24ce1b3ddf454fd59c33c
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450363B2
Reaction notes
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