5-bromo-2-methyl-N-(2-methylpropyl)aniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using the same method as in Example 19-(ii), 4-fluoro-benzene boronic acid was reacted with 5-bromo-2-methyl-N-(2-methylpropyl)aniline to give 4′-fluoro-4-methyl-N-(2-methylpropyl)biphenyl-3-amine (yield: 83%).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7.44 g (40.0 mmol) of 5-bromo-2-methylaniline, 8.22 g (60.0 mmol) of 1-bromo-2-methyl propane, 8.99 g (60.0 mmol) of sodium iodide and 8.29 g (60.0 mmol) of potassium carbonate were stirred in a DMF solvent at 70° C. for 22 hours. To the reaction mixture was added water and extracted with ethyl acetate. The organic layer was separated, washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting crude product was separated and purified using silica gel column chromatography to give 5.92 g of 5-bromo-2-methyl-N-(2-methylpropyl)aniline (yield: 61%). extracted with ethyl acetate The organic layer was separated washed with a saturated sodium chloride solution dried over anhydrous sodium sulfate concentrated under reduced pressure The resulting crude product was separated purified