Sulfuric Acid → 4-(3-Bromophenyl)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinoline
Reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[CH2:4][N:5]([CH3:16])[CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1)O.S(=O)(=O)(O)O.[OH-].[Na+]>ClCCl>[Br:15][C:11]1[CH:10]=[C:9]([CH:7]2[C:17]3[C:3](=[C:2]([Cl:1])[CH:20]=[C:19]([Cl:21])[CH:18]=3)[CH2:4][N:5]([CH3:16])[CH2:6]2)[CH:14]=[CH:13][CH:12]=1Participants
Conditions
- Temperature
- 2.5 °C
Procedure
Into a 500-mL 3-necked round-bottom flask, was placed a solution of 2-((2,4-dichlorobenzyl)(methyl)amino)-1-(3-bromophenyl)ethanol (25 g, 64.27 mmol, 1.00 equiv) in dichloromethane (100 mL). This was followed by the addition of sulfuric acid (100 mL) dropwise with stirring at 0-5° C. The resulting solution was stirred for 4 h at room temperature. The resulting solution was diluted with of ice water. The pH value of the solution was adjusted to 8 with sodium hydroxide. The resulting solution was extracted with 3×300 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was re-crystallized from petroleum ether:ethyl acetate in the ratio of 8:1. This resulted in 15 g (63%) of 4-(3-bromophenyl)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinoline as a white solid.
Workup
- customInto a 500-mL 3-necked round-bottom flask, was placed
- stirringThe resulting solution was stirred for 4 h at room temperature
- extractionThe resulting solution was extracted with 3×300 mL of dichloromethane
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
- customThe crude product was re-crystallized from petroleum ether
- customThis resulted in 15 g (63%) of 4-(3-bromophenyl)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinoline as a white solid
Sources & evidence
- ORD record
- ord-459be014ac134f97a8cd24e8cface6b3
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541448B2
Reaction notes
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