Nitric Acid → (2-Nitrophenyl)boronic acid

HRID 2224371Notes

Reaction equation

HRID 2224371 reaction equation
[C:1]1([B:7]([OH:9])[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:10]([O-])([OH:12])=[O:11]>C(OC(=O)C)(=O)C>[N+:10]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[B:7]([OH:9])[OH:8])([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 66827Phenylboronic Acid

Product 1

HCID 2773548(2-Nitrophenyl)boronic acidYield 15%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of phenyl boronic acid (5.0 g, 41 mmol) in acetic anhydride (50 mL) at −15° C. was treated with nitric acid (2.5 mL) dropwise over 30 minutes maintaining a temperature below −10° C. The reaction was allowed to warm to room temperature overnight, then poured onto ice. The resulting solution was concentrated to 25 mL and water (50 mL) was added. The mixture was again concentrated. This procedure was repeated five times. The solid that developed was filtered and dried. The crude product was purified by flash chromatography (SiO2, 2% EtOH/CH2Cl2) to afford the desired product (1.0 g, 15%).

Workup

  1. temperaturemaintaining a temperature below −10° C
  2. additionpoured onto ice
  3. concentrationThe resulting solution was concentrated to 25 mL and water (50 mL)
  4. additionwas added
  5. concentrationThe mixture was again concentrated
  6. filtrationThe solid that developed was filtered
  7. customdried
  8. customThe crude product was purified by flash chromatography (SiO2, 2% EtOH/CH2Cl2)

Sources & evidence

ORD record
ord-9901047aa7704cc4bd15a9ea7f1d1e8b
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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