Potassium Nitrate → 2-Fluoro-5-methoxycarbonyloxy-4-methylnitrobenzene

HRID 2064133Notes

Reaction equation

HRID 2064133 reaction equation
[C:1](=[O:13])([O:11][CH3:12])[O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[CH3:10].[N+:14]([O-])([O-:16])=[O:15].[K+]>S(=O)(=O)(O)O>[C:1](=[O:13])([O:11][CH3:12])[O:2][C:3]1[CH:8]=[C:7]([N+:14]([O-:16])=[O:15])[C:6]([F:9])=[CH:5][C:4]=1[CH3:10]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 106790444-Fluoro-2-methylphenyl Methoxyformate

Product 1

HCID 144216192-Fluoro-5-methoxycarbonyloxy-4-methylnitrobenzeneYield 94.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

4-Fluoro-2-methylphenyl methyl carbonate (D14) (2.5 mmol, 468 mg) was dissolved in concentrated sulphuric acid under argon and cooled to 0° C. KNO3 (2.5 mmol, 253 mg, 1 eq) was then added cautiously while keeping the temperature around 0° C. The mixture was then allowed to stir for 2 h while warming up to room temperature, then it was poured onto ice cautiously and extracted with ether twice. Organics were combined, dried on MgSO4 and concentrated under reduced pressure to give the title compound as a light brown solid (2.36 mmol, 540 mg, 94% yield). 1H NMR (CDCl3) 7.92 (1H, d), 7.18 (1H, d), 3.95 (3H, s), 2.33 (3H, s).

Workup

  1. customthe temperature around 0° C
  2. temperaturewhile warming up to room temperature
  3. additionit was poured onto ice cautiously
  4. extractionextracted with ether twice
  5. customdried on MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-18eca95a12dc46c1a73ca2a19fc6eb12
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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