2,6-Difluoro-3-methoxyBenzaldehyde

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

Procedure: Butyl-[1-(2,6-difluoro-3-methoxy-phenyl)-meth-(E)-ylidene]-amine was prepared from 2,6-difluoro-3-methoxybenzaldehyde, N-butylamine and p-toluenesulphonic acid in analogy to Example 186a): red oil; MS (ISP): 228.4 ([M+H]+, 100%).

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

Procedure: Butyl-[1-(2,6-difluoro-3-methoxy-phenyl)-meth-(E)-ylidene]-amine was prepared from 2,6-difluoro-3-methoxybenzaldehyde, N-butylamine and p-toluenesulphonic acid in analogy to Example 186a): red oil; MS (ISP): 228.4 ([M+H]+, 100%).

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

Procedure: Butyl-[1-(2,6-difluoro-3-methoxy-phenyl)-meth-(E)-ylidene]-amine was prepared from 2,6-difluoro-3-methoxybenzaldehyde, N-butylamine and p-toluenesulphonic acid in analogy to Example 186a): red oil; MS (ISP): 228.4 ([M+H]+, 100%).

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

Procedure: Prepared in analogy to Example 72(a)-(e) from 2,6-difluoro-3-methoxybenzaldehyde, N-butylamine and p-toluenesulphonic acid in toluene, then treatment with 3 equivalents of ethylmagnesium bromide and manganese(II) chloride in tetrahydrofuran and ether followed by chromatography on silical gel, then treatment with boron tribromide in dichloromethane, then treatment with iodoethane and potassium carbonate in N,N-dimethylformamide, then treatment with in situ prepared (1-trityl-1H-imidazol-4-yl)-magnesium halide in dichloromethane, and then treatment with triethylsilane and trifluoroacetic acid in dichloromethane in a pressure tube at 70° C. for 16 h. Amorphous white solid. MS (ISP): 259.3 ([M+H]+).

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 600 mg (3.48 mmol) of 2,6-difluoro-3-methoxybenzaldehyde (CAS 149949-30-4) in 8 ml of ethanol at 0° C. was admixed with 65.9 mg (1.74 mmol) of sodium borohydride in portions. After stirring at 0° C. for 30 min, the reaction mixture was quenched with water and extracted three times with methyl tert-butyl ether. The combined organic extracts were washed with water and saturated aqueous sodium chloride solution, and dried with a phase separation cartridge. The solvent was drawn off to dryness under reduced pressure, which gave 550 mg (89% of theory) of the target compound. at 0° C. the reaction mixture was quenched with water extracted three times with methyl tert-butyl ether The combined organic extracts were washed with water and saturated aqueous sodium chloride solution dried with a phase separation cartridge gave 550 mg (89% of theory) of the target compound

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

Procedure: Butyl-[1-(2,6-difluoro-3-methoxy-phenyl)-meth-(E)-ylidene]-amine was prepared from 2,6-difluoro-3-methoxybenzaldehyde, N-butylamine and p-toluenesulphonic acid in analogy to Example 186a): red oil; MS (ISP): 228.4 ([M+H]+, 100%).