Nitric Acid → (2-Nitrophenyl)boronic acid

HRID 496105Notes

Reaction equation

HRID 496105 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(Cl)Cl.CCO>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

5

Reactant 3

HCID 944Nitric AcidHCID 66827Phenylboronic AcidHCID 21584144Dichloromethane ethanol

Product 1

HCID 2773548(2-Nitrophenyl)boronic acidYield 35.1%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of phenylboronic acid (10 g; 82 mmol) in acetic acid anhydride (100 ml) at −15° C. was added fuming HNO3 (5 ml; 120 mmol) over 30 min such that reaction temperature was kept below −10° C. The reaction mixture was allowed to warm up to rt. and left with stirring over night. The reaction mixture was poured onto ice and concentrated to 50 ml. The remanense was then re-evaporated 5 times from additional H2O (100 ml) and finally filtered to give 7.1 g crude product as a mixture of isomers. Column chromatography (CH2Cl2/EtOH=10/0.5) gave 4.8 g (35%) pure product as an oil.

Workup

  1. customsuch that reaction temperature
  2. customwas kept below −10° C
  3. waitand left
  4. additionThe reaction mixture was poured onto ice
  5. concentrationconcentrated to 50 ml
  6. customThe remanense was then re-evaporated 5 times from additional H2O (100 ml)
  7. filtrationfinally filtered
  8. customto give 7.1 g crude product
  9. additionas a mixture of isomers

Sources & evidence

ORD record
ord-14933110c088495a9d6af4396176c827
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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