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

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Reaction Steps

A 250 ml round bottomed flask fitted with refrigerator, under nitrogen stream, is loaded with 3-bromoaniline (16 ml), dimethylformamide (80 ml), 2-methyl-3-butyn-2-ol (21.3 ml), 1,1,3,3-tetramethyl guanidine (20.3 ml), CuCl (0.044 g), PdCl2 (0.156 g) and triphenyl phosphine (0.925 g), in this order. The mixture is heated to 70°-75° C., keeping this temperature until completion of the reaction. H2O (250 ml) and CH2Cl2 (100 ml) are added at a temperature of 35°-30° C. The organic phase is dried, then evaporated to dryness. The residue is purified by chromatography to obtain 18.5 g of 4-(3-aminophenyl)-2-methyl-3-butyn-2-ol. Yield: 71% with HPLC purity ≥99%.

Provenance & Evidence