1-(3-aminophenyl)-2,2-dimethylpropan-1-one

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combine 1-(3-iodo-phenyl)-2,2-dimethyl-propan-1-one (2.0 g, 8.3 mmol), benzophenone imine (1.7 mL, 1.2 equiv.), racemic BINAP (0.23 g, 4.5 mol %), NaOtBu (1.1 g, 1.4 equiv.), and THF (30 mL). De-gas thoroughly with nitrogen then add bis(dibenzylideneacetone) palladium (0.14 g, 3 mol %) and place under nitrogen. Heat the reaction at 50° C. overnight. The next morning add approximately 8 mL 5 N HCl (aq) and heat for an additional hour at 50° C. Let cool to room temperature then dilute with ethyl acetate and make basic with 1 N NaOH (aq). Wash organics with aqueous saturated sodium chloride. Dry over magnesium sulfate, filter and concentrate in vacuo. Purify by silica chromatography (Hex→9:1 Hex:EtOAc→4:1 Hex:EtOAc) to give a yellow residue (1.2 g, 82%). MS (ES), m/z 178 (M+1). De-gas thoroughly with nitrogen Heat the reaction at 50° C. overnight Let cool to room temperature Dry over magnesium sulfate filter concentrate in vacuo Purify by silica chromatography (Hex→9:1 Hex:EtOAc→4:1 Hex:EtOAc)