Sulfuric Acid → 4-(4-Bromophenyl)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 45654Notes

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][C:12]([Br:15])=[CH:11][CH:10]=1)O.OS(O)(=O)=O>ClCCl>[Br:15][C:12]1[CH:13]=[CH:14][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:10][CH:11]=1

Participants

Conditions

Temperature: 20 °C

Procedure

Into a 50-mL 3-necked round-bottom flask, was placed a solution of 2-((2,4-dichlorobenzyl)(methyl)amino)-1-(4-bromophenyl)ethanol (1.0 g, 2.57 mmol, 1.00 equiv) in dichloromethane (3 mL). This was followed by the addition of conc.H2SO4 (2 mL) dropwise with stirring at 0-5° C. The resulting solution was stirred for 3 h at 20° C. The reaction was then quenched by the addition of water/ice. The pH value of the solution was adjusted to 9 with sodium hydroxide. The resulting solution was extracted with dichloromethane (2×30 mL) and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 0.9 g of the title compound which was used without further purification. MS (ES, m/z): 372 [M+H]+.

Workup

customInto a 50-mL 3-necked round-bottom flask, was placed
additionThis was followed by the addition of conc
customThe reaction was then quenched by the addition of water/ice
extractionThe resulting solution was extracted with dichloromethane (2×30 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-800002959568456c882e8a28078ae2f8
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541448B2

Reaction notes

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