2-Fluoroaniline → 4-Bromo-2-fluoroaniline
Reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12]>C(Cl)Cl>[Br:1][C:15]1[CH:14]=[CH:13][C:11]([NH2:12])=[C:10]([F:9])[CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
160 Parts of solid N-bromosuccinimide were added in portions over a 2 hour period to a solution of 100 parts of 2fluoroaniline in 400 parts of methylene chloride cooled to 0° C. After stirring for 20 minutes, the dark red mixture was washed four times; 200 parts of cold water were used for each washing. The red organic phase was dried with anhydrous sodium sulfate and evaporated under 300 mm. Hg to 164 parts of brown, oily 4-bromo-2-fluoroaniline, nD25 : 1.5885.
Workup
- washthe dark red mixture was washed four times
- dry with materialThe red organic phase was dried with anhydrous sodium sulfate
- customevaporated under 300 mm. Hg to 164 parts of brown, oily 4-bromo-2-fluoroaniline
Sources & evidence
- ORD record
- ord-4e5993c2e7034e2a85379f3972d9c6d4
- Source dataset
- uspto-grants-1976_11
- Patent number
- US03992189
Reaction notes
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