Hydrochloric Acid → HCID 67439835, compound

HRID 1255614Notes

Reaction equation

HRID 1255614 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-202d9a4d95fe4c5e9c7507c17ccb7726
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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