Nitric Acid → 1,3-Dibromo-5-fluoro-2-methoxy-4-nitrobenzene
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Br:9])[C:3]=1[O:10][CH3:11].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:12]([O-:14])=[O:13])=[C:4]([Br:9])[C:3]=1[O:10][CH3:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 4 °C
Procedure
To a stirred solution of c.H2SO4 (740 mL) at 0 to 5° C. was added 1,3-dibromo-5-fluoro-2-methoxybenzene (223.3 g, 0.786 mol). A solution of fuming nitric acid (90%, 38 mL, 0.815 mol) in c.H2SO4 (740 mL) was added dropwise, maintaining the temperature between 0 and 5° C. The reaction mixture was stirred at 3 to 5° C. for 2 hours, quenched into ice (2.2 kg) and extracted with dichloromethane (3×2 L). The combined dichloromethane extracts were washed with saturated aqueous NaHCO3 solution (2×2 L), dried over Na2SO4, filtered and the filter cake washed with DCM (3×400 mL). The filtrate was concentrated in vacuo at 40° C. to give 1,3-Dibromo-5-fluoro-2-methoxy-4-nitrobenzene as a pale orange crystalline solid (244.9 g, 95%).
Workup
- temperaturemaintaining the temperature between 0 and 5° C
- customquenched into ice (2.2 kg)
- extractionextracted with dichloromethane (3×2 L)
- washThe combined dichloromethane extracts were washed with saturated aqueous NaHCO3 solution (2×2 L)
- dry with materialdried over Na2SO4
- filtrationfiltered
- washthe filter cake washed with DCM (3×400 mL)
- concentrationThe filtrate was concentrated in vacuo at 40° C.
Sources & evidence
- ORD record
- ord-417708790e7142aea303520839496f61
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07429598B2
Reaction notes
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