1-Bromo-2-methylpropane → 4-t-butyl-2-fluoro-N-methoxycarbonylaniline

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2-Fluoro-N-methoxycarbonylaniline (500 mg, 3.11 mmol) was dissolved in methylene chloride (20 mL) to prepare a solution. Anhydrous aluminum chloride (986 mg, 7.77 mmol) was added to the solution, and the mixture was stirred at 40° C. for 20 min. Thereafter, the reaction solution was cooled to room temperature. A solution of isobutyl bromide (1.60 mL, 15.5 mmol) in a methylene chloride solution (6 mL) was added dropwise to the cooled reaction mixture while bubbling argon gas over a period of 10 min. The mixture was stirred for one hr. Water was added thereto, followed by separation of an organic layer. The organic layer was washed with water and was dried over anhydrous magnesium sulfate. The solvent was then removed from the dried organic layer by distillation to give 779 mg of 4-t-butyl-2-fluoro-N-methoxycarbonylaniline as a crude product. The crude product was further subjected to separation and purification by column chromatography on silica gel to give 433 mg of 4-t-butyl-2-fluoro-N-methoxycarbonylaniline (yield 64.0%, 4-t-butyl form: 5-t-butyl form=88:12).

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