5-(bromomethyl)furan-2-carbaldehyde

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

Procedure: To a solution of 0.20 g (1.1 mmol) of 5-(bromomethyl)furan-2-carboxaldehyde in anhydrous dioxane (10 ml) are added 261 μL (0.24 g, 2.3 mmol) of 1-methylpiperazine. The mixture is stirred at room temperature for 30 min. The precipitate formed is filtered and rinsed with dioxane. The filtrate is concentrated, dissolved in dichloromethane, and washed in water. The organic phase is dried over magnesium sulfate, filtered, and concentrated. The residue obtained is purified by chromatography on silica (eluent: 7N NH4OH in MeOH/CH2Cl2, 5:95) to yield 0.12 g (55%) of 5-((4-methylpiperazine-1-yl)methyl)furan-2-carboxaldehyde in the form of an orange solid. The precipitate formed is filtered rinsed with dioxane The filtrate is concentrated dissolved in dichloromethane washed in water The organic phase is dried over magnesium sulfate filtered concentrated The residue obtained is purified by chromatography on silica (eluent: 7N NH4OH in MeOH/CH2Cl2, 5:95)

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3.4 g (26.7 mmol) of 5-(hydroxymethyl)furan-2-carboxaldehyde and 7.78 g (29.4 mmol) of triphenylphosphine in 300 ml of dichloromethane at −5° C. are added 5.28 g (29.4 mmol) of N-bromosuccinimide in 10 min. The mixture is stirred at −5° C. for 30 min. The mixture is then concentrated and the residue is purified by chromatography on silica (cyclohexane/AcOet: 7:3) to yield 4.38 g (87%) of 5-(bromomethyl)furan-2-carboxaldehyde in the form of a brown solid. The mixture is then concentrated the residue is purified by chromatography on silica (cyclohexane/AcOet: 7:3)

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

Procedure: To a solution of 0.20 g (1.1 mmol) of 5-(bromomethyl)furan-2-carboxaldehyde in anhydrous dioxane (10 ml) are added 261 μL (0.24 g, 2.3 mmol) of 1-methylpiperazine. The mixture is stirred at room temperature for 30 min. The precipitate formed is filtered and rinsed with dioxane. The filtrate is concentrated, dissolved in dichloromethane, and washed in water. The organic phase is dried over magnesium sulfate, filtered, and concentrated. The residue obtained is purified by chromatography on silica (eluent: 7N NH4OH in MeOH/CH2Cl2, 5:95) to yield 0.12 g (55%) of 5-((4-methylpiperazine-1-yl)methyl)furan-2-carboxaldehyde in the form of an orange solid. The precipitate formed is filtered rinsed with dioxane The filtrate is concentrated dissolved in dichloromethane washed in water The organic phase is dried over magnesium sulfate filtered concentrated The residue obtained is purified by chromatography on silica (eluent: 7N NH4OH in MeOH/CH2Cl2, 5:95)

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3.4 g (26.7 mmol) of 5-(hydroxymethyl)furan-2-carboxaldehyde and 7.78 g (29.4 mmol) of triphenylphosphine in 300 ml of dichloromethane at −5° C. are added 5.28 g (29.4 mmol) of N-bromosuccinimide in 10 min. The mixture is stirred at −5° C. for 30 min. The mixture is then concentrated and the residue is purified by chromatography on silica (cyclohexane/AcOet: 7:3) to yield 4.38 g (87%) of 5-(bromomethyl)furan-2-carboxaldehyde in the form of a brown solid. The mixture is then concentrated the residue is purified by chromatography on silica (cyclohexane/AcOet: 7:3)

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

Procedure: To a solution of 0.20 g (1.1 mmol) of 5-(bromomethyl)furan-2-carboxaldehyde in anhydrous dioxane (10 ml) are added 261 μL (0.24 g, 2.3 mmol) of 1-methylpiperazine. The mixture is stirred at room temperature for 30 min. The precipitate formed is filtered and rinsed with dioxane. The filtrate is concentrated, dissolved in dichloromethane, and washed in water. The organic phase is dried over magnesium sulfate, filtered, and concentrated. The residue obtained is purified by chromatography on silica (eluent: 7N NH4OH in MeOH/CH2Cl2, 5:95) to yield 0.12 g (55%) of 5-((4-methylpiperazine-1-yl)methyl)furan-2-carboxaldehyde in the form of an orange solid. The precipitate formed is filtered rinsed with dioxane The filtrate is concentrated dissolved in dichloromethane washed in water The organic phase is dried over magnesium sulfate filtered concentrated The residue obtained is purified by chromatography on silica (eluent: 7N NH4OH in MeOH/CH2Cl2, 5:95)

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3.4 g (26.7 mmol) of 5-(hydroxymethyl)furan-2-carboxaldehyde and 7.78 g (29.4 mmol) of triphenylphosphine in 300 ml of dichloromethane at −5° C. are added 5.28 g (29.4 mmol) of N-bromosuccinimide in 10 min. The mixture is stirred at −5° C. for 30 min. The mixture is then concentrated and the residue is purified by chromatography on silica (cyclohexane/AcOet: 7:3) to yield 4.38 g (87%) of 5-(bromomethyl)furan-2-carboxaldehyde in the form of a brown solid. The mixture is then concentrated the residue is purified by chromatography on silica (cyclohexane/AcOet: 7:3)