Hydrogen Bromide → HCID 18615650, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH:9]C(=O)OCC)=[C:4]([N+:15]([O-:17])=[O:16])[C:3]=1[F:18].Br>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH2:9])=[C:4]([N+:15]([O-:17])=[O:16])[C:3]=1[F:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
Ethyl 4-chloro-3,6-difluoro-2-nitrophenylcarbamate (XLI) (0.9 g, 3.2 mmol) was mixed with acetic acid (30 ml) and hydrobromic acid (48%, 25 ml), the mixture was stirred at 150° C. for 4 hr and then the volume reduced to half by evaporation Ethyl acetate (50 ml) was added and the solution was washed with water (15 ml×3) and dried over sodium sulfate. The product was purified by column chromatography (silica gel, hexane) (0.56 g). 1H NMR (CDCl3, 300 MHz) 5.73 (2H, br), 7.24 (1H, dd, J=6.1, 6.1 Hz) ppm.
Workup
- customthe volume reduced to half by evaporation Ethyl acetate (50 ml)
- additionwas added
- washthe solution was washed with water (15 ml×3)
- dry with materialdried over sodium sulfate
- customThe product was purified by column chromatography (silica gel, hexane) (0.56 g)
Sources & evidence
- ORD record
- ord-37620650c78f40b1b46d32bb61528601
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06355799B1
Reaction notes
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