Aluminum(III) Chloride → HCID 21966430, compound

HRID 365533Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([N:9]([CH:16]([CH3:18])[CH3:17])[C:10](=[O:15])[CH:11]=[C:12]([CH3:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[CH3:8].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:12]([CH3:14])([CH3:13])[CH2:11][C:10](=[O:15])[N:9]2[CH:16]([CH3:18])[CH3:17])=[CH:6][C:7]=1[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

3-Methyl-but-2-enoic acid (3-bromo-4-methyl-phenyl)-isopropyl-amide (Compound 42, 50 g, 161.2 mmol) was dissolved in dichloromethane (800 mL) and the solution was cooled to 0° C. and treated with AlCl3 (75.23 g, 564.2 mmol). The suspension was stirred at 0° C. for 1 hour and at room temperature for 1 hour and the reaction was quenched with ice. After 10% aqueous HCl was added, the layers were separated and the aqueous layer extracted twice with dichloromethane. The combined organic layers were washed with water and brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was filtered by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.38) to give the title compound as an oil:

Workup

customthe reaction was quenched with ice
additionAfter 10% aqueous HCl was added
customthe layers were separated
extractionthe aqueous layer extracted twice with dichloromethane
washThe combined organic layers were washed with water and brine
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
filtrationThe residue was filtered by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.38)

Sources & evidence

ORD record: ord-f68cd28e4cb94b81ac98f3a240e061fa
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127382

Reaction notes

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