Hydrochloric Acid → HCID 67439835, compound

HRID 1664312Notes

Reaction equation

HRID 1664312 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]3[B:15]([OH:16])[O:14][CH2:13][C:12]=3[CH:17]=2)=[CH:5][C:4]=1[C:20]([O:22]C)=[O:21])#[N:2].[OH-].[Na+].Cl>CO>[C:20]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][C:3]=1[C:1]#[N:2])[O:7][C:8]1[CH:9]=[CH:10][C:11]2[B:15]([OH:16])[O:14][CH2:13][C:12]=2[CH:17]=1)([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67440088HCID 67440088, compound

Product 1

HCID 67439835HCID 67439835, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-(4-Cyano-3-methoxycarbonylphenoxy)-1-hydroxy-2,1-benzoxaborole (5.25 g, 17.0 mmol) and 1 M NaOH (50 mL) in methanol (150 mL) was stirred at room temperature for 1 h. The mixture was acidified with 6 M HCl and extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (ethyl acetate to 3:1 chloroform/methanol) followed by trituration with ethyl acetate to give 5-(3-carboxy-4-cyanophenoxy)-1-hydroxy-2,1-benzoxaborole (810 mg, 16%)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel chromatography (ethyl acetate to 3:1 chloroform/methanol)

Sources & evidence

ORD record
ord-83cc5a9aa1e04afdbc50c5b37668fe0e
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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