Nitric Acid → 3,5-Difluoro-4-nitrophenol
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.[N+:10]([O-])([OH:12])=[O:11]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[C:7]=1[N+:10]([O-:12])=[O:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3,5-difluorophenol (10 g, 76.9 mmol) in CH2Cl2 at 0° Celsius was added 4.9 mL of 70% nitric acid dropwise. After addition was complete, the reaction was allowed to warm to room temperature and stirred for 1 hour. The reaction was poured into a separatory funnel and washed once with 750 mL water. The organic layer was dried with Na2SO4, filtered and concentrated to dryness. The resulting residue was purified via FCC to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 6.81-6.67 (m, 2H), 3.40 (bs, 1H).
Workup
- additionAfter addition
- additionThe reaction was poured into a separatory funnel
- washwashed once with 750 mL water
- dry with materialThe organic layer was dried with Na2SO4
- filtrationfiltered
- concentrationconcentrated to dryness
- customThe resulting residue was purified via FCC
Sources & evidence
- ORD record
- ord-400a7eec424642a88a5b1ad16b0f90f4
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952177B2
Reaction notes
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