Hydrogen Bromide → 1-(2-Bromoethyl)-2-fluoro-4-nitrobenzene
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12]O.[BrH:14].S(=O)(=O)(O)O>O>[Br:14][CH2:12][CH2:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
2-(2-Fluoro-4-nitrophenyl)ethanol (0.89 g, 4.8 mmol) was added to a stirred solution of 48% aqueous hydrobromic acid (0.77 g, 9.62 mmol) and concentrated sulfuric acid (0.25 mL) under cooling. The reaction mixture was heated to 100° C. for 3 h. The reaction mixture was diluted with water (25 mL) and was extracted with ethyl acetate (3×25 mL). The combined organic layer was washed with brine (25 mL) and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the crude compound. The crude product was purified by CC (eluent: 5% ethyl acetate in n-hexane) to afford 1-(2-bromoethyl)-2-fluoro-4-nitrobenzene (1 g, 85%).
Workup
- temperatureunder cooling
- extractionwas extracted with ethyl acetate (3×25 mL)
- washThe combined organic layer was washed with brine (25 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customto afford the crude compound
- customThe crude product was purified by CC (eluent: 5% ethyl acetate in n-hexane)
Sources & evidence
- ORD record
- ord-20ee4d57031142de85f8112f098c11df
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946204B2
Reaction notes
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