Nitric Acid → HCID 21877560, compound

HRID 724431Notes

Reaction equation

HRID 724431 reaction equation
[N+:1]([O-:4])(O)=[O:2].C(O)(C(F)(F)F)=O.[CH3:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[B:20]([OH:22])[OH:21]>>[CH3:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([N+:1]([O-:4])=[O:2])=[CH:15][C:14]=1[B:20]([OH:21])[OH:22]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 6422Trifluoroacetic acidHCID 4198739(2,4-Dimethylphenyl)boronic acid

Product 1

HCID 21877560HCID 21877560, compoundYield 47%

Conditions

Temperature
-35 °C

Procedure

To fuming nitric acid (1 ml) cooled to −40° C. was added TFA (1 ml). The resulting mixture was allowed to warm slightly to −35° C. and 2,4-dimethyl phenyl boronic acid (150 mg, 1 mmol) was added in one portion. After 1 h, ice was added and the heterogenous mixture was filtered. The resulting solid was suspended in Et2O and extracted with 3N NaOH (aq) (1 ml) then water (2 ml). The aqueous phase was acidified with 3N HCl (aq) (1 ml) and back extracted with EtOAc (3×5 ml). The pooled organics were washed with brine, dried with Na2SO4 decanted and concentrated to give 2,4-dimethyl-5-nitro-phenyl boronic acid (93 mg, 47%). LCMS (ESI+) [M+H]/z Calc'd 196. found 196.

Workup

  1. additionice was added
  2. filtrationthe heterogenous mixture was filtered
  3. extractionextracted with 3N NaOH (aq) (1 ml)
  4. extractionback extracted with EtOAc (3×5 ml)
  5. washThe pooled organics were washed with brine
  6. dry with materialdried with Na2SO4
  7. customdecanted
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a34296e8e7e546ddaf785231156dcdae
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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