3-Bromoaniline → 3-Butyn-2-ol, 4-(3-aminophenyl)-2-methyl-

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Reaction Steps

In a 3-liter 4-neck flask provided with a mechanical stirrer there are introduced—in the order—64.0 g (0.50 mol, 1.0 eq.) of 4-hydroxy-4-methyl-2-pentinoic acid, 5.7 g of Pd(OAc)2 (5% mol), 24 g of XPhos (2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl; 10% mol) and 378 g (1.5 mol, 3 eq. mol.) of TBAF (Tetra-n-butylammonium fluoride). The mixture is dissolved, under Argon atmosphere, in 2 L of distilled anhydrous THF. 55 ml of 3-Bromoaniline (d=1.585 g/mL, 0.5 mol, 1.0 eq. mol.) are added to this solution.

Provenance & Evidence