Ethanol → Ethyl 2-Amino-4-fluorobenzoate

HRID 38159

Reaction equation

HRID 38159 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

Reactant 3

HCID 702EthanolHCID 24386Thionyl Chloride2×HCID 27249674-Fluoroanthranilic acid

Product 1

HCID 14233600Ethyl 2-Amino-4-fluorobenzoateYield 94%

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

  1. temperatureThe reaction mixture was refluxed for 4 days total
  2. concentrationconcentrated
  3. additiondiluted with EtOAc
  4. washwashed with 2N NaOH
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c780703793d34af5989b04b2ccbe9181
Source dataset
uspto-grants-2013_09
Patent number
US08524721B2

Linked notes

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