Nitric Acid → HCID 59678151, compound

HRID 251578Notes

Reaction equation

HRID 251578 reaction equation
[CH:1]([C:4]1[C:9]([B:10]([OH:12])[OH:11])=[C:8]([CH3:13])[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[N+:14]([O-])([OH:16])=[O:15]>O>[CH:1]([C:4]1[C:9]([B:10]([OH:12])[OH:11])=[C:8]([CH3:13])[C:7]([N+:14]([O-:16])=[O:15])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 52988141[2-Methyl-6-(propan-2-yl)phenyl]boronic acid

Product 1

HCID 59678151HCID 59678151, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-35 °C

Procedure

6-Isopropyl-2-methylbenzeneboronic acid (8 g) is added portionwise over 1 hour to 90% HNO3 (50 mL) at −40° C., maintaining an internal temperature below −30° C. After addition, the mixture is stirred at −40 to −30° C. for 15 minutes, then poured onto ice, and diluted with water. The solid is collected by filtration, washed with water and dried to give 6-isopropyl-2-methyl-3-nitrobenzeneboronic acid as a white solid. 1H NMR (DMSO-d6) 7.78 (d, 2H), 7.30 (d, 2H), 2.85 (m, 1H), 2.38 (s, 3H), 1.15 (d, 6H).

Workup

  1. temperaturemaintaining an internal temperature below −30° C
  2. additionAfter addition
  3. additionpoured onto ice
  4. filtrationThe solid is collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e8e747b7bca24abba34dd53d05bc793f
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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