Nitric Acid → 4-Bromo-6-fluoro-3-methyl-2-nitrophenol
Reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.[N+:11]([O-])([OH:13])=[O:12]>C(O)(=O)C.C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([OH:9])=[C:6]([N+:11]([O-:13])=[O:12])[C:7]=1[CH3:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-bromo-2-fluoro-5-methylphenol (1.26 g, 6.15 mmol) in acetic acid (4 mL) and chloroform (2 mL) was added concentrated nitric acid (0.392 mL, 6.15 mmol) at −10° C. and the mixture was stirred at room temperature for 18 hours and then at 50° C. for 20 minutes (−50% desired product). The reaction mixture was diluted with ethyl acetate, then washed with water and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, concentrated and purified on silica gel (0-15% ethyl acetate/n-hexane) to afford 4-bromo-6-fluoro-3-methyl-2-nitrophenol (0.69 g, 2.76 mmol, 44.9% yield) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) d=7.57 (d, 1 H), 2.54 (d, J=1.2 Hz, 3 H); LC/MS (m/z) ES−: 247.96 (M−1).
Sources & evidence
- ORD record
- ord-06b8712e77f3447dbc4d981c129a2bdd
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609653B2
Reaction notes
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