Acetic Anhydride → 2-Acetamidophenylboronic acid

HRID 1647375Notes

Reaction equation

HRID 1647375 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[B:8]([OH:10])[OH:9].[C:11](OC(=O)C)(=[O:13])[CH3:12]>O1CCOCC1>[C:11]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[B:8]([OH:10])[OH:9])(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 2773216(2-Aminophenyl)boronic acid

Product 1

HCID 27377892-Acetamidophenylboronic acidYield 83.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of o-aminophenylboronic acid (6.73 g, 49.1 mmoles) in dioxane (100 ml) is added acetic anhydride (25.1 g, 246 mmoles). The reaction is heated at 100° C. for 17 hours. After cooling, the reaction volatiles are removed under reduced pressure to leave a thick yellow gel, which after chromatography affords o-N-acetylaminophenylboronic acid (7.33 g).

Workup

  1. temperatureAfter cooling
  2. customthe reaction volatiles
  3. customare removed under reduced pressure
  4. customto leave a thick yellow gel, which after chromatography

Sources & evidence

ORD record
ord-dfa39f9d19974ea6bb4af0b0a8ab1370
Source dataset
uspto-grants-1995_07
Patent number
US05431842

Reaction notes

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