Ethanol → Ethyl 4-amino-2,5-difluorobenzoate

HRID 630423Notes

Reaction equation

HRID 630423 reaction equation
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:12])[CH:3]=1.[CH2:13](O)[CH3:14].O.C(=O)(O)[O-]>Cl>[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([O:8][CH2:13][CH3:14])=[O:7])=[C:4]([F:12])[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 769Bicarbonate IonHCID 962WaterHCID 201514774-Amino-2,5-difluorobenzoic acid2×

Product 1

HCID 67469350Ethyl 4-amino-2,5-difluorobenzoateYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-amino-2,5-difluorobenzoic acid (intermediate 137; 2.7 g; 0.015 mol) in hydrogen chloride 1.25 mL in ethanol (91 mL, 0.113 mol) was stirred for 24 hours at 60° C. The solvent was removed under reduced pressure and the crude obtained was treated with water and solid bicarbonate to obtain a basic pH, after few minutes stirring an extraction with ethyl acetate was done. The organic layer was washed with brine, dried and the solvent was removed under reduced pressure to give the title compound as a white solid (92%), which was used in the next step without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude obtained
  3. customto obtain a basic pH
  4. extractionan extraction with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-224375bdd5c14bbb9ad8027a3cb5c851
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

Loading…