Boron trifluoride etherate → Ethyl 4-amino-3-fluorobenzoate

HRID 1156099Notes

Reaction equation

HRID 1156099 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[F:11].B(F)(F)F.[CH3:16][CH2:17]OCC>C(O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:16][CH3:17])=[O:7])=[CH:4][C:3]=1[F:11]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 99714-Amino-3-fluorobenzoic acid

Product 1

HCID 20536493Ethyl 4-amino-3-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 15.0 g of 4-amino-3-fluorobenzoic acid 150 ml of anhydrous ethyl alcohol and 5 ml of boron trifluoride etherate is heated to reflux for 20 hours. Most of the solvent is then removed and 200 ml of water added and the mixture extracted with chloroform. The chloroform extract is washed with an aqueous solution of sodium bicarbonate dried over sodium sulfate and the solvent evaporated to yield an off-white solid which upon recrystallization from ethanolhexane yields ethyl 4-amino-3-fluorobenzoate as a white solid.

Workup

  1. temperatureto reflux for 20 hours
  2. customMost of the solvent is then removed
  3. addition200 ml of water added
  4. extractionthe mixture extracted with chloroform
  5. extractionThe chloroform extract
  6. washis washed with an aqueous solution of sodium bicarbonate
  7. dry with materialdried over sodium sulfate
  8. customthe solvent evaporated
  9. customto yield an off-white solid which
  10. customupon recrystallization from ethanolhexane

Sources & evidence

ORD record
ord-8f5693d42bc94a76b9c2e48420ebe534
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

Loading…