4-iodo-3-methoxyaniline

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

Procedure: 4-Iodo-3-methoxy-phenylamine (3.17 g, 12.7 mmol) and ethynyl-trimethyl-silane (3.5 mL, 25 mmol) in dry acetonitrile were purged with nitrogen and treated with TEA (17.6 mL, 127 mmol), CuI (123 mg, 0.635 mmol) and Pd(Ph3P)2Cl2 (447 mg, 0.635 mmol). The reaction was stirred at room temperature for 2 h. The volatiles were evaporated, the residue was taken up with EtOAc (200 mL), washed with water (50 mL), dried over sodium sulfate and purified by flash chromatography on silica gel (hexane/EtOAc 55/45) to afford the title compound (1.86 g, 66%). The volatiles were evaporated washed with water (50 mL) dried over sodium sulfate purified by flash chromatography on silica gel (hexane/EtOAc 55/45)

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

Procedure: 1-Iodo-2-methoxy-4-nitro-benzene (6.01 g, 21.54 mmol) in absolute ethanol (127 mL) was cooled with an ice bath and treated with SnCl2 (18.83 g, 99.31 mmol). The bath was removed and the mixture was stirred at room temperature for 4 h then poured into ice (300 mL), stirred and treated carefully with saturated aqueous sodium bicarbonate (250 mL) (pH 7-8). The solid was filtered with suction and the panel washed thoroughly with EtOAc (500 mL and 4×200 mL). The aqueous layer was separated, dried over sodium sulphate and evaporated. Purification of the crude by flash chromatography on silica gel (hexane/EtOAc 1/1) furnished the title compound (3.17 g, 59%). The bath was removed then poured into ice (300 mL) stirred treated carefully with saturated aqueous sodium bicarbonate (250 mL) (pH 7-8) The solid was filtered with suction the panel washed thoroughly with EtOAc (500 mL and 4×200 mL) The aqueous layer was separated dried over sodium sulphate evaporated Purification of the crude by flash chromatography on silica gel (hexane/EtOAc 1/1)