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

HRID 1160060Notes

Reaction equation

HRID 1160060 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-olYield 87.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Formylphenylboronic acid (25 g, 0.167 mol) was added to a cooled solution of sodium hydroxide (7.0 g, 0.175 mol, 1.05 eq) in 83 mL of water at 10° C. Nitromethane (10.17 g, 1 eq) was added to this solution and then warmed to room temperature with stirring. This mixture was stirred for 3.5 hours. The reaction was then cooled in an ice bath and acidified with 3M HCl to a pH of 2. A white precipitate was collected and filtered, washed with water and air dried to obtain 28 g (87%) of 3-(nitromethyl)benzo[c][1,2]oxaborol-1(3H)-ol (off-white solid).

Workup

  1. stirringThis mixture was stirred for 3.5 hours
  2. temperatureThe reaction was then cooled in an ice bath
  3. customA white precipitate was collected
  4. filtrationfiltered
  5. washwashed with water and air
  6. customdried

Sources & evidence

ORD record
ord-f6e0108fa3a74e8a9dc2b2f9d18d7145
Source dataset
uspto-grants-2010_10
Patent number
US07816344B2

Reaction notes

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