Acetic Acid → HCID 58148233, compound

HRID 1913689Notes

Reaction equation

HRID 1913689 reaction equation
[F:1][C:2]1([F:17])[C:10]2[C:5](=[CH:6][C:7]([OH:14])=[C:8]([N+:11]([O-])=O)[CH:9]=2)[C:4]([F:16])([F:15])[O:3]1.C(O)(=O)C>[Fe].O>[NH2:11][C:8]1[CH:9]=[C:10]2[C:5]([C:4]([F:16])([F:15])[O:3][C:2]2([F:1])[F:17])=[CH:6][C:7]=1[OH:14]

Participants

5

Reactant 2

HCID 176Acetic Acid2×HCID 66880971HCID 66880971, compound

Product 1

HCID 58148233HCID 58148233, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 6.8 g of 1,1,3,3-tetrafluoro-5-hydroxy-6-nitro-1,3-dihydroisobenzofuran and 20 ml of acetic acid was added dropwise to a mixture, which was heated to 80° C., of 7.8 g of electrolytic iron, 20 ml of acetic acid and 20 ml of water, and then the reaction mixture was stirred for one hour. The mixture was cooled to room temperature, and then water was added, followed by extraction with ethyl acetate twice. The combined organic layers were washed with water, a saturated aqueous solution of sodium hydrogencarbonate, and a saturated sodium chloride solution, and dried over magnesium sulfate. Activated carbon was added, followed by filtration through Celite™. The filtrates were concentrated under reduced pressure to give 4.43 g of 6-amino-1,1,3,3-tetrafluoro-5-hydroxy-1,3-dihydroisobenzofuran.

Workup

  1. additionwas added dropwise to a mixture, which
  2. extractionfollowed by extraction with ethyl acetate twice
  3. washThe combined organic layers were washed with water
  4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, and a saturated sodium chloride solution, and dried over magnesium sulfate
  5. additionActivated carbon was added
  6. filtrationfollowed by filtration through Celite™
  7. concentrationThe filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-fb9f1ecf159840c4a425e8776bf3a61f
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

Loading…