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

HRID 1930417Notes

Reaction equation

HRID 1930417 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([O-:12])=[O:11].[K+]>OS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]([F:8])=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 967432-Bromo-5-fluorotoluene

Product 1

HCID 100369831-Bromo-4-fluoro-2-methyl-5-nitrobenzeneYield 53.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-bromo-4-fluoro-2-methylbenzene (30 g, 0.16 mol) in cone. H2SO4 (200 mL) was added KNO3 (16.1 g, 0.16 mol) at 0° C. portion wise. After the resulting mixture was stirred at 0° C. for 30 min, the reaction was poured into ice water and extracted with EtOAc (3×100 mL). The combined organic layers were washed with saturated Na2CO3 solution and brine, dried, filtered and concentrated to give 1-bromo-4-fluoro-2-methyl-5-nitrobenzene (20 g, 53.6% yield). 1HNMR (300 Hz, DMSO-d6): δ 8.15 (d, J=7.2 Hz, 1 H), 7.52 (d, J=12 Hz, 1 H), 2.35 (s, 3 H).

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. washThe combined organic layers were washed with saturated Na2CO3 solution and brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-eb7d42e5c0154f91a4cdbb135ff2c373
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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