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

HRID 339612Notes

Reaction equation

HRID 339612 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-eb8b3af4dc7d49f5ad04821e83703cbb
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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