[Mg].II.[Cl:4][C:5]1[CH:6]=[C:7](Br)[CH:8]=[CH:9][C:10]=1[Cl:11].[CH3:13][N:14]1[CH2:19][C:18]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH2:16][CH2:15]1.Cl>CCOCC>[CH3:13][N:14]1[CH2:15][CH2:16][CH:17]([C:7]2[CH:8]=[CH:9][C:10]([Cl:11])=[C:5]([Cl:4])[CH:6]=2)[CH:18]([C:20]([O:22][CH3:23])=[O:21])[CH2:19]1To magnesium (5.5 g, 229 mmol) and a few crystals of iodine in anhydrous ether (20 mL) was added 3,4-dichlorobromobenzene (46.4 g, 206 mmol) in anhydrous ether (200 mL) at a rate sufficient to keep the reaction at reflux. After the addition was completed the reaction was heated at reflux for another 15 min. The reaction was cooled to −20° C. and arecoline (16 g, 103 mmol) in anhydrous ether (200 mL) was added over 20 min while keeping the temperature at −20° C. The reaction was stirred for another 2 hour at −20° C. and then heated to 0° C. Hydrochloric acid (4 N, 80 mL) was added and the pH adjusted to 1 using concentrated hydrochloric acid. The organic phase was separated off and the pH adjusted to 9 with concentrated ammonia. Extraction with ether (2×200 mL)afforded 24.6 g of the title compound as a brownish oil.
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