Nitric Acid → 6-Nitro-3-nitromethyl-3H-benzo[c][1,2]oxaborol-1-ol

HRID 339627Notes

Reaction equation

HRID 339627 reaction equation
[N+:1]([CH2:4][CH:5]1[O:9][B:8]([OH:10])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]1=2)([O-:3])=[O:2].[N+:15]([O-])([OH:17])=[O:16]>>[N+:15]([C:12]1[CH:13]=[CH:14][C:6]2[CH:5]([CH2:4][N+:1]([O-:3])=[O:2])[O:9][B:8]([OH:10])[C:7]=2[CH:11]=1)([O-:17])=[O:16]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 574518233-Nitromethyl-3H-benzo[c][1,2]oxaborol-1-ol

Product 1

HCID 574518396-Nitro-3-nitromethyl-3H-benzo[c][1,2]oxaborol-1-ol

Procedure

3-Nitromethyl-3H-benzo[c][1,2]oxaborol-1-ol (20.0 g, 104 mmol) was added in small portions with stirring over 2 h to fuming HNO3 (200 mL) at −45° C. (bath temp). The cold reaction mixture was then poured into crushed ice and allowed to warm to rt. The aqueous phase was extracted with EtOAc. The EtOAc phase was concentrated in vacuo and the residue was poured into crushed ice. The precipitate was filtered and washed with H2O. The solid was dissolved in EtOAc, dried (Na2SO4), and concentrated in vacuo to yield the title compound: yield (14.3 g, 58%).

Workup

  1. customThe cold reaction mixture
  2. additionwas then poured
  3. custominto crushed ice
  4. extractionThe aqueous phase was extracted with EtOAc
  5. concentrationThe EtOAc phase was concentrated in vacuo
  6. additionthe residue was poured
  7. custominto crushed ice
  8. filtrationThe precipitate was filtered
  9. washwashed with H2O
  10. dissolutionThe solid was dissolved in EtOAc
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e47588c698ad4d4ea265ea5d15ddcaf0
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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