2,3-Dichlorobenzoyl chloride → (7-bromo-2-ethyl-1H-indol-3-yl)-(2,3-dichlorophenyl)methanone
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([CH2:11][CH3:12])=[CH:7]2.C[Mg]I.[Cl:16][C:17]1[C:18]([Cl:26])=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=[O:21].[NH4+].[Cl-]>CCOCC.C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([CH2:11][CH3:12])=[C:7]2[C:20]([C:19]1[CH:23]=[CH:24][CH:25]=[C:17]([Cl:16])[C:18]=1[Cl:26])=[O:21]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
3.45 g of 7-bromo-2-ethyl-1H-indole are placed under nitrogen in 30 ml of ether and the mixture is cooled to +3° C.; 5.1 ml of methylmagnesium iodide in 20 ml of ether and then 5.9 g of dichlorobenzoyl chloride in 30 ml of ether are added. 10 ml of THF are added and the mixture is allowed to return to AT and is stirred for 3 hours. The medium is poured onto a saturated NH4Cl solution and is then extracted with ether. The organic phase is washed with a 10% HCl solution, a 10% NaOH solution, water and an NaCl solution. It is dried and evaporated and then the residue is chromatographed on silica while eluting with an AcOEt/cyclohexane (3/7, v/v) mixture. 2.18 g of the expected compound are obtained.
Workup
- temperaturethe mixture is cooled to +3° C.
- extractionis then extracted with ether
- washThe organic phase is washed with a 10% HCl solution
- customIt is dried
- customevaporated
- customthe residue is chromatographed on silica
- washwhile eluting with an AcOEt/cyclohexane (3/7
Sources & evidence
- ORD record
- ord-866e5f4114dc4410ba1f7c436f733c5e
- Source dataset
- uspto-grants-2006_02
- Patent number
- US06995184B2
Reaction notes
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