Nitric Acid → 2-Bromo-1,3-dimethyl-4-nitrobenzene

HRID 475296Notes

Reaction equation

HRID 475296 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 684712-Bromo-m-xylene

Product 1

HCID 123959052-Bromo-1,3-dimethyl-4-nitrobenzeneYield 37%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a mixture of 2-bromo-1,3-dimethylbenzene (5.0 g, 27.03 mmol) in sulfuric acid (98%, 40 mL) at −10° C. was added dropwise a solution of nitric acid (68%, 2.74 g, 27.03 mmol) in sulfuric acid (98%, 10 mL). After the reaction was complete the mixture was stirred at −10° C. for 1 h. The reaction mixture was poured onto ice (200 g) the resulting solid filtered, washed with water, and dried in vacuo. The crude was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (100:1) as eluting solvent to afford 2.3 g (37%) of 2-bromo-1,3-dimethyl-4-nitrobenzene as yellow solid (298): 1H NMR (500 MHz, DMSO-d6): δ 7.79 (d, J=8.5, 1H), 7.43 (d, J=8.5, 1H), 2.47 (s, 3H), 2.44 (s, 3H).

Workup

  1. additionThe reaction mixture was poured onto ice (200 g) the resulting solid
  2. filtrationfiltered
  3. washwashed with water
  4. customdried in vacuo
  5. customThe crude was purified by SiO2 chromatography
  6. washeluting with petroleum ether/EtOAc (100:1)
  7. washas eluting solvent

Sources & evidence

ORD record
ord-88235139d7854863baa524cc10693fd4
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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