Nitric Acid → 1-Bromo-2,5-dimethyl-4-nitrobenzene

HRID 2361247Notes

Reaction equation

HRID 2361247 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([OH:12])=[O:11].S(=O)(=O)(O)O>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 11121Benzene, 2-bromo-1,4-dimethyl-

Product 1

HCID 8258081-Bromo-2,5-dimethyl-4-nitrobenzeneYield 36.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a slurry of 2-bromo-1,4-dimethylbenzene (10.13 g, 54.7 mmol) in acetic acid (44 mL) at 8° C. (inner temperature) was added a solution of nitric acid (6 mL, 134 mmol) in sulfuric acid (22 mL, 413 mmol) over 45 min; temperature rose to 10° C. After 1 hr, the reaction mixture was poured into ice and stirred, filtered and washed with water to give a light yellow solid. This was triturated with EtOH (10 mL) to give the desired product (4.550 g, 19.78 mmol, 36.1% yield) as an off-white solid.

Workup

  1. customrose to 10° C
  2. additionthe reaction mixture was poured into ice
  3. filtrationfiltered
  4. washwashed with water
  5. customto give a light yellow solid
  6. customThis was triturated with EtOH (10 mL)

Sources & evidence

ORD record
ord-4d82a265161f4851a7b76108efac0643
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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