Ethanol → Ethyl 2-Amino-4-fluorobenzoate
Reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH2:16](O)[CH3:17]>>[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:16][CH3:17])=[O:5]Participants
4
Procedure
To a chilled solution of 2-amino-4-fluorobenzoic acid (1.57 g, 10.1 mmol) in absolute ethanol (20 mL) was added neat thionyl chloride (4.4 mL, 60 mmol). The reaction mixture was refluxed for 4 days total, with addition of more SOCl2 (8 mL, 110 mmol), then concentrated, diluted with EtOAc, washed with 2N NaOH, dried and concentrated in vacuo to give ethyl 2-amino-4-fluorobenzoate (1.73 g, 94%).
Workup
- temperatureThe reaction mixture was refluxed for 4 days total
- concentrationconcentrated
- additiondiluted with EtOAc
- washwashed with 2N NaOH
- customdried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c780703793d34af5989b04b2ccbe9181
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524721B2
Reaction notes
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