Hydrogen Bromide → 2,2',4'-Trifluoro-3-hydroxybiphenyl-4-carbaldehyde
Reaction equation
Br.[F:2][C:3]1[C:8]([O:9]C)=[C:7]([CH:11]=[O:12])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[F:20]>C(O)(=O)C>[F:2][C:3]1[C:8]([OH:9])=[C:7]([CH:11]=[O:12])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[F:20]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
48% hydrobromic acid (22.0 mL) was added at room temperature to an acetic acid (120 mL) solution of 2,2′,4′-trifluoro-3-methoxybiphenyl-4-carbaldehyde (5.14 g), and the mixture was stirred at 120 C for 16 hours in a nitrogen atmosphere. Then, the solvent was distilled off under reduced pressure. The obtained residue was neutralized with a 1 M aqueous sodium hydroxide solution at room temperature, followed by extraction with ethyl acetate. The organic layer was separated, then washed with water and saturated saline in this order, and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was passed through a short silica gel column, and the solvent was distilled off under reduced pressure to obtain the title compound (4.60 g).
Workup
- distillationThen, the solvent was distilled off under reduced pressure
- customwas neutralized with a 1 M aqueous sodium hydroxide solution at room temperature
- extractionfollowed by extraction with ethyl acetate
- customThe organic layer was separated
- washwashed with water and saturated saline in this order
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-24ba71b0c5c34c7a969370783ff6c054
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120777B2
Reaction notes
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