Potassium Nitrate → 1-Bromo-5-fluoro-2-methyl-4-nitrobenzene

HRID 1897661Notes

Reaction equation

HRID 1897661 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([O-:12])=[O:11].[K+]>S(=O)(=O)(O)O.O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 2

HCID 24434Potassium NitrateHCID 740162-Bromo-4-fluorotoluene

Product 1

HCID 534032861-Bromo-5-fluoro-2-methyl-4-nitrobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-bromo-4-fluoro-1-methylbenzene (5 g, 26.4 mmol) dissolved in conc. sulfuric acid (20 mL) was added potassium nitrate (2.67 g, 26.4 mmol) in sulfuric acid (5 mL) at 0° C. After stirring at 0° C. for 1 hr, the reaction was diluted with water, extracted with ethyl acetate (3×40 mL). The combined organic phases were washed with saturated sodium bicarbonate solution and brine sequentially, and then dried over Na2SO4. The crude product obtained after concentration was purified by silica gel column chromatography with mixed solvent hexanes/EtOAc (95/5) to afford 1-bromo-5-fluoro-2-methyl-4-nitrobenzene as an orange solid. 1H NMR (400 MHz, chloroform-d) δ 7.93 (d, 1H, J=7.6 Hz), 7.50 (d, 1H, J=10 Hz), 2.43 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate (3×40 mL)
  2. washThe combined organic phases were washed with saturated sodium bicarbonate solution and brine sequentially
  3. dry with materialdried over Na2SO4
  4. customThe crude product obtained
  5. concentrationafter concentration
  6. customwas purified by silica gel column chromatography with mixed solvent hexanes/EtOAc (95/5)

Sources & evidence

ORD record
ord-7dedfc3fba4f401d8f6a5f97b0b3dde6
Source dataset
uspto-grants-2013_08
Patent number
US08519129B2

Reaction notes

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