Aniline → HCID 57529294, compound

Participants

Reaction Steps

A solution of palladium(II) acetate (1.1 mg, 0.005 mmol) and xantphos (8.9 mg, 0.015 mmol) in toluene (8 ml) was stirred at room temperature for 5 min in a sealable tube purged with nitrogen, methyl 3-bromo-5-iodobenzoate (340 mg, 1.0 mmol) and aniline (111.8 mg, 1.2 mmol) were added and let stir for 5 more min, Sodium tert-butoxide (134.6 mg, 1.4 mmol) was then added and the mixture was stirred at room temperature for 5 min before heated up to 80° C. for 3 h. The reaction mixture was cooled down to RT and ether (containing 1% triethylamine) was added, passed through a celite column, dried over sodium sulfate and concentrated under vacuum to give the crude product which was used directly in the next reaction without further purification: HPLC retention time: 2.123 min (method A). MS (ESI) (M+H)+ 292.07.

Provenance & Evidence