Boron trifluoride etherate → Ethyl 4-Amino-2-fluorobenzoate

HRID 1156095Notes

Reaction equation

HRID 1156095 reaction equation
C([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([F:14])[CH:6]=1)(=O)C.B(F)(F)F.[CH3:19][CH2:20]OCC>C(O)C>[NH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][CH2:19][CH3:20])=[O:10])=[C:7]([F:14])[CH:6]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 130413704-Acetamido-2-fluorobenzoic acid

Product 1

HCID 10797532Ethyl 4-Amino-2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10.0 g of 4-acetamido-2-fluorobenzoic acid, 100 ml of ethyl alcohol and 2.0 ml of boron trifluoride etherate is heated under reflux for 22 hours. The solvent is slowly removed by distillation as an equal amount of fresh ethyl alcohol is added. After 200 ml of solvent has been removed, the remainder is evaporated at reduced pressure. The residue is dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate, dried and the solvent then evaporated to yield a solid. Recrystallization of the solid from ethanol-hexane yields ethyl 4-amino-2-fluorobenzoate.

Workup

  1. temperatureunder reflux for 22 hours
  2. customThe solvent is slowly removed by distillation as an equal amount of fresh ethyl alcohol
  3. additionis added
  4. customAfter 200 ml of solvent has been removed
  5. customthe remainder is evaporated at reduced pressure
  6. dissolutionThe residue is dissolved in ethyl acetate
  7. washwashed with saturated aqueous sodium bicarbonate
  8. customdried
  9. customthe solvent then evaporated
  10. customto yield a solid
  11. customRecrystallization of the solid from ethanol-hexane

Sources & evidence

ORD record
ord-b7df3b592cee4ad9a707e91fb97d8101
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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