Hydrochloric Acid → 2, 3-Difluoro-1-methoxy-4-(4-pentylbicyclo[2.2.2]octyl)benzene

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A solution of 1-bromo-4-pentylbicyclo[2.2.2]octane (6 g, 23 mmol) in sieve-dried nitrobenzene (100 cm3) is added dropwise to a stirred solution of 2, 3-difluoro-4-methoxybenzene (6 g, 23 mmol) and anhydrous iron(III)chloride (1.2 g, 9 mmol) in sieve-dried nitrobenzene (100 cm3) maintained at 80° C. throughout the addition and overnight. The cooled solution is added to a small volume of hydrochloric acid and stirred for 20 min. The organic layer is separated off and steam-distilled to yield a solid residue. This is taken up in dichloromethane and dried (MgSO4). The raw product is crystallised from ethanol to yield the desired 2, 3-difluoro-1-methoxy-4-(4-pentylbicyclo[2.2.2]octyl)benzene (3.2 g, 44%)

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