(3,5-difluoro-4-methoxyphenyl)methanamine

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

Procedure: A mixture of 2-fluoronitrobenzene (0.82 g, 5.8 mmole), 3,5-difluoro-4-methoxybenzylamine, (3.0 g, 17.3 mmole) and ammonium acetate (0.5 g) was reacted substantially as described in 1C above to yield 1.7 g, (100%) of the title compound as orange crystals. was reacted substantially

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

Procedure: A mixture of 2-fluoronitrobenzene (0.82 g, 5.8 mmole), 3,5-difluoro-4-methoxybenzylamine, (3.0 g, 17.3 mmole) and ammonium acetate (0.5 g) was reacted substantially as described in 1C above to yield 1.7 g, (100%) of the title compound as orange crystals. was reacted substantially

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

Procedure: The reaction of 3,5-difluoro-4-methoxybenzaldehyde methoxime, (7 g, 35 mmole) and 0.98M borane in tetrahydrofuran (46 ml) substantially as described in 1B above produced 3 g, (50%) of the title compound as a clear oil.

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

Procedure: A mixture of 2-fluoronitrobenzene (0.82 g, 5.8 mmole), 3,5-difluoro-4-methoxybenzylamine, (3.0 g, 17.3 mmole) and ammonium acetate (0.5 g) was reacted substantially as described in 1C above to yield 1.7 g, (100%) of the title compound as orange crystals. was reacted substantially

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

Procedure: The reaction of 3,5-difluoro-4-methoxybenzaldehyde methoxime, (7 g, 35 mmole) and 0.98M borane in tetrahydrofuran (46 ml) substantially as described in 1B above produced 3 g, (50%) of the title compound as a clear oil.

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3,5-difluoro-4-methoxybenzylamine (8.7 g, 0.05 mole) and triethylamine (15.5 ml, 0.11 mole) in 50 ml of tetrahydrofuran was added dropwise to a solution of thiophosgene (4.2 ml, 0.055 mole) in 50 ml of tetrahydrofuran with cooling to -10° C. over a period of twenty minutes. The mixture was stirred at 25° C. for 2.75 hours and then filtered. The filtrate was treated with charcoal, filtered, and evaporated to an oil. The oil was diluted with hexane:ethyl acetate (90:10) and purified on a flash silica column using hexane:ethyl acetate (90:10) as the eluant to yield 9.2 g (79%) of 3,5-difluoro-4-methoxybenzyl isothiocyanate. filtered The filtrate was treated with charcoal filtered evaporated to an oil The oil was diluted with hexane:ethyl acetate (90:10) purified on a flash silica column

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

Procedure: A mixture of 2-fluoronitrobenzene (0.82 g, 5.8 mmole), 3,5-difluoro-4-methoxybenzylamine, (3.0 g, 17.3 mmole) and ammonium acetate (0.5 g) was reacted substantially as described in 1C above to yield 1.7 g, (100%) of the title compound as orange crystals. was reacted substantially

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

Procedure: The reaction of 3,5-difluoro-4-methoxybenzaldehyde methoxime, (7 g, 35 mmole) and 0.98M borane in tetrahydrofuran (46 ml) substantially as described in 1B above produced 3 g, (50%) of the title compound as a clear oil.