Hydrochloric Acid → 3-Nitromethyl-3H-benzo[c][1,2]oxaborol-1-ol

HRID 1160058Notes

Reaction equation

HRID 1160058 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[B:9]([OH:11])[OH:10])=O.[OH-].[Na+].[N+:14]([CH3:17])([O-:16])=[O:15].Cl>O>[N+:14]([CH2:17][CH:1]1[O:11][B:9]([OH:10])[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]1=2)([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 2921892-Formylphenylboronic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-formylphenylboronic acid (3 g, 20.0 mmol) was added to solution of sodium hydroxide (850 mg, 1.05 eq) in 10 mL of water at 10° C. To this suspension was added nitromethane (1.1 mL, 1 eq) and then warmed to room temperature with stirring. After 30 minutes, the reaction was cooled in an ice bath and acidified with 3M HCl. A white precipitate was filtered and air dried to 3.2 g (82.9%) of 3-(nitromethyl)benzo[c][1,2]oxaborol-1(3H)-ol.

Workup

  1. temperaturethe reaction was cooled in an ice bath
  2. filtrationA white precipitate was filtered
  3. dry with materialair dried to 3.2 g (82.9%) of 3-(nitromethyl)benzo[c][1,2]oxaborol-1(3H)-ol

Sources & evidence

ORD record
ord-2c7da1ab2a77472daf8d09b8dacad1e6
Source dataset
uspto-grants-2010_10
Patent number
US07816344B2

Reaction notes

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