2-Fluorobenzoyl chloride → 2-Di-n-propylamino-8-(2'-fluorobenzoyl)-1,2,3,4-tetrahydronaphthalene

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2-Di-n-propylamino-8-bromo-1,2,3,4-tetrahydronaphthalene (1.0 g; 3.22 mmol) dissolved in THF (25 ml) was cooled to -78° C., and 2.5 ml of n-butyllithium (1.27M in hexane) were added. After one hour, o-fluorobenzoyl chloride (0.38 ml, 3.22 mmol) was added. The mixture was stirred for 10 minutes at -78° C. after which the reaction was quenched by addition of water at -78° C. The reaction was made basic with NaOH and extracted three times with methylene chloride. The basic extract was dried (Na2SO4) and concentrated to give 2.0 g of crude residue. Purification of this material by flash silica gel chromatography using 1:1 ether:hexane containing a trace of ammonium hydroxide as solvent provided 2-di-n-propylamino-8-(2'-fluorobenzoyl)-1,2,3,4-tetrahydronaphthalene (340 mg).

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