3-Bromoanisole → 1-(3-Methoxyphenyl)piperidine-4-carbonitrile

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piperidine-4-carbonitrile (0.353 g, 3.21 mmol); 1-bromo-3-methoxybenzene (0.339 mL, 2.67 mmol) and diacetoxypalladium (0.120 g, 0.53 mmol) were thoroughly placed under an inert atmoshere. To this was added 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.037 g, 0.11 mmol); LITHIUM BIS(TRIMETHYLSILYL)AMIDE (6.15 mL, 6.15 mmol) and toluene (10 mL). The resultant mixture was stirred overnight at 100 °C (suspect that it did not need overnight. Equal vol of DCM was added and the reaction mixture filtered. Removal of the solvent under reduced pressure gave a dark brown gum. The crude product was purified by flash Silica chromatography {CombiFlash Companion - Presearch Ltd}, column size = 12 g , flow rate = 30 ml / min, elution gradient 0 to 30% EtOAc in isohexane over 10 minutes {excluding lead in & wash etc.}. Pure fractions were evaporated to dryness to afford 1-(3-methoxyphenyl)piperidine-4-carbonitrile (0.315 g, 54.5 %) as a tan brown solid.

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