Reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=1N)([CH3:3])[CH3:2].N([O-])=O.[Na+].CCCCCC.[BrH:22]>O.[Cu]Br>[Br:22][C:5]1[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:4]=1[CH:1]([CH3:3])[CH3:2]Participants
7
Conditions
- Temperature
- 5 °C
Procedure
2-isopropyl-6-methylanilin (14.9 g, 0.1 mol) was solved in conc hydrobromic acid (40 ml) and the mixture was cooled to 5° C. Sodium nitrite (7.0 g, 0.1 mol) in water (15 ml) was added so that the temperature was below 10° C. A solution of copper(I)bromide in conc hydrobromic acid (10 ml) was added to the reaction mixture and the temperature was allowed to raise to room temperature. The mixture was stirred for 1 h. at room temperature and 30 min at 40° C. Hexane was added and the organic layer was separated and evaporated under reduced pressure. Purification by column chromatography on silica gel using hexane as eluent gave 6.9 g (32%) of the title compound as an oil.
Workup
- customwas below 10° C
- temperatureto raise to room temperature
- customthe organic layer was separated
- customevaporated under reduced pressure
- customPurification by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-6b859450d5604b5fb1782cac550c23a7
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313137B1
Linked notes
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