Sodium Chloride → 7-bromo-2-ethyl-1H-indole
Reaction equation
[Mg].Br[C:3]([CH2:5][CH3:6])=[CH2:4].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-])=O.[Na+].[Cl-]>C1COCC1>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:9]=1[NH:14][C:3]([CH2:5][CH3:6])=[CH:4]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
2.4 g of magnesium are placed in a round-bottomed flask and the magnesium is covered with 10 ml of THF. 1 g of 2-bromo-1-butene, then 10 ml of THF and then again 12.5 g of 2-bromo-1-butene in 30 ml of THF are added. The reaction medium is observed to warm up and then it is heated at 60° C. for 30 minutes after the end of the addition reaction. The mixture is subsequently cooled to −20° C., 20 ml of THF are added and then 6.7 g of 2-bromonitrobenzene are added at −20° C. The mixture is allowed to return to AT. The reaction medium is poured onto 200 ml of a saturated NaCl solution. Extraction is carried out with ether, the extracts are then evaporated and the residue is taken up in DCM. The organic phase is washed with water and then with a saturated NaCl solution. It is dried and evaporated and then the residue is chromatographed on silica while eluting with a cyclohexane/AcOEt (9.5/0.5, v/v) mixture. 3.45 g of the expected compound are obtained.
Workup
- temperatureto warm up
- additionafter the end of the addition reaction
- temperatureThe mixture is subsequently cooled to −20° C.
- extractionExtraction
- customthe extracts are then evaporated
- washThe organic phase is washed with water
- customIt is dried
- customevaporated
- customthe residue is chromatographed on silica
- washwhile eluting with a cyclohexane/AcOEt (9.5/0.5
Sources & evidence
- ORD record
- ord-a97595312546450ca0c9737b930206f5
- Source dataset
- uspto-grants-2006_02
- Patent number
- US06995184B2
Reaction notes
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