Hydrogen Bromide → 4-Bromo-3-fluoro-2-hydroxybenzaldehyde
Reaction equation
Br.[Br:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([O:11]C)[C:4]=1[F:13]>C(O)(=O)C>[Br:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([OH:11])[C:4]=1[F:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
48% Hydrobromic acid (254 mL) was added to a solution of 4-bromo-3-fluoro-2-methoxybenzaldehyde (52.3 g) in acetic acid (350 mL) at room temperature. The mixture was stirred at 120° C. under nitrogen atmosphere for 16 hours and concentrated in vacuo. The residue was diluted with ethyl acetate and water. The mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was triturated with diisopropyl ether and collected by filtration to give the title compound (34.6 g).
Workup
- concentrationconcentrated in vacuo
- additionThe residue was diluted with ethyl acetate and water
- extractionThe mixture was extracted with ethyl acetate
- customThe organic layer was separated
- washwashed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was triturated with diisopropyl ether
- filtrationcollected by filtration
Sources & evidence
- ORD record
- ord-0c4f100283fd452c8d91cd68fb394f58
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09353108B2
Reaction notes
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