Hydrochloric Acid → 6,8-Difluoro-7-hydroxy-3-carboxycoumarin

HRID 355406Notes

Reaction equation

HRID 355406 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[OH:12])[O:8][C:7](=[O:14])[C:6]([C:15]([O:17]CC)=[O:16])=[CH:5]2.[OH-].[K+].Cl>C1COCC1.CO.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[OH:12])[O:8][C:7](=[O:14])[C:6]([C:15]([OH:17])=[O:16])=[CH:5]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 44335997HCID 44335997, compound

Product 1

HCID 189423216,8-Difluoro-7-hydroxy-3-carboxycoumarinYield 94%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 14 (100 mg, 0.37 mmol) and KOH (70 mg, 85%, 1.1 mmol) in 7 mL of THF/MeOH/H2O (5:5:1) is heated at 60° C. for 2 hours. The reaction is poured into 50 mL 5% HCl and extracted with EtOAc (40 mL×2), washed with brine (30 mL), dried over anhydrous MgSO4, and concentrated in vacuo to yield 81 mg (94%) of Compound 15 as a green powder.

Workup

  1. extractionextracted with EtOAc (40 mL×2)
  2. washwashed with brine (30 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f03a910d7c1840d1bbb99cb897ca7032
Source dataset
uspto-grants-1998_11
Patent number
US05830912

Reaction notes

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