5-chloro-2-hydroxy-4-methoxybenzaldehyde

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

Procedure: The above prepared 5-chloro-2-hydroxy-4-methoxy-benzaldehyde (example 36, step 1, 1.050 g, 5.63 mmol) was dissolved in 15 mL of abs. THF and treated at −15° C. with PhMgBr (15.5 mL of 1M [THF], 2.7 eq.) and the mixture kept at this temperature for 0.5 h. Careful pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=7/3) yielded 1.39 g of the title compound as light brown oil. was dissolved in 15 mL of abs Careful pouring ice/NH4Cl, twofold extraction with AcOEt washing with water drying over sodium sulfate, and evaporation of the solvents

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

Procedure: The above prepared 5-chloro-2-hydroxy-4-methoxy-benzaldehyde (example 36, step 1, 1.050 g, 5.63 mmol) was dissolved in 15 mL of abs. THF and treated at −15° C. with PhMgBr (15.5 mL of 1M [THF], 2.7 eq.) and the mixture kept at this temperature for 0.5 h. Careful pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=7/3) yielded 1.39 g of the title compound as light brown oil. was dissolved in 15 mL of abs Careful pouring ice/NH4Cl, twofold extraction with AcOEt washing with water drying over sodium sulfate, and evaporation of the solvents

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

Procedure: The above prepared 5-chloro-2-hydroxy-4-methoxy-benzaldehyde (0.845 g, 4.53 mmol) was dissolved in 10 mL of abs. THF and treated at −15° C. with iPrMgCl (4.98 mL of 2M [THF], 2.2 eq.) and the mixture kept at this temperature for 0.5 h. Careful pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents left 1.090 g of the title compound as light brown oil, almost perfectly pure according to TLC and NMR. was dissolved in 10 mL of abs Careful pouring ice/NH4Cl, twofold extraction with AcOEt washing with water drying over sodium sulfate, and evaporation of the solvents left 1.090 g of the title compound as light brown oil

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

Procedure: The above prepared 5-chloro-2-hydroxy-4-methoxy-benzaldehyde (0.845 g, 4.53 mmol) was dissolved in 10 mL of abs. THF and treated at −15° C. with iPrMgCl (4.98 mL of 2M [THF], 2.2 eq.) and the mixture kept at this temperature for 0.5 h. Careful pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents left 1.090 g of the title compound as light brown oil, almost perfectly pure according to TLC and NMR. was dissolved in 10 mL of abs Careful pouring ice/NH4Cl, twofold extraction with AcOEt washing with water drying over sodium sulfate, and evaporation of the solvents left 1.090 g of the title compound as light brown oil

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Hydroxy-4-methoxy-benzaldehyde (0.974 g, 6.40 mmol) was dissolved in 10 mL of acetonitrile and treated with N-chlorosuccinimide (0.983 g, 1.15 eq.) and ammonium nitrate (0.102 g, 0.20 eq.), and the mixture was warmed to 70° C. for roughly 5 h. Evaporation of the solvent, followed by flash chromatography (SiO2, heptane/AcOEt=85/15), and direct crystallization from heptane/AcOEt, produced then 0.259 g of the title compound as white crystals. Evaporation of the solvent followed by flash chromatography (SiO2, heptane/AcOEt=85/15), and direct crystallization from heptane/AcOEt produced

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Hydroxy-4-methoxy-benzaldehyde (0.974 g, 6.40 mmol) was dissolved in 10 mL of acetonitrile and treated with N-chlorosuccinimide (0.983 g, 1.15 eq.) and ammonium nitrate (0.102 g, 0.20 eq.), and the mixture was warmed to 70° C. for roughly 5 h. Evaporation of the solvent, followed by flash chromatography (SiO2, heptane/AcOEt=85/15), and direct crystallization from heptane/AcOEt, produced then 0.259 g of the title compound as white crystals. Evaporation of the solvent followed by flash chromatography (SiO2, heptane/AcOEt=85/15), and direct crystallization from heptane/AcOEt produced

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

Procedure: The above prepared 5-chloro-2-hydroxy-4-methoxy-benzaldehyde (example 36, step 1, 1.050 g, 5.63 mmol) was dissolved in 15 mL of abs. THF and treated at −15° C. with PhMgBr (15.5 mL of 1M [THF], 2.7 eq.) and the mixture kept at this temperature for 0.5 h. Careful pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=7/3) yielded 1.39 g of the title compound as light brown oil. was dissolved in 15 mL of abs Careful pouring ice/NH4Cl, twofold extraction with AcOEt washing with water drying over sodium sulfate, and evaporation of the solvents

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

Procedure: The above prepared 5-chloro-2-hydroxy-4-methoxy-benzaldehyde (0.845 g, 4.53 mmol) was dissolved in 10 mL of abs. THF and treated at −15° C. with iPrMgCl (4.98 mL of 2M [THF], 2.2 eq.) and the mixture kept at this temperature for 0.5 h. Careful pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents left 1.090 g of the title compound as light brown oil, almost perfectly pure according to TLC and NMR. was dissolved in 10 mL of abs Careful pouring ice/NH4Cl, twofold extraction with AcOEt washing with water drying over sodium sulfate, and evaporation of the solvents left 1.090 g of the title compound as light brown oil

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Hydroxy-4-methoxy-benzaldehyde (0.974 g, 6.40 mmol) was dissolved in 10 mL of acetonitrile and treated with N-chlorosuccinimide (0.983 g, 1.15 eq.) and ammonium nitrate (0.102 g, 0.20 eq.), and the mixture was warmed to 70° C. for roughly 5 h. Evaporation of the solvent, followed by flash chromatography (SiO2, heptane/AcOEt=85/15), and direct crystallization from heptane/AcOEt, produced then 0.259 g of the title compound as white crystals. Evaporation of the solvent followed by flash chromatography (SiO2, heptane/AcOEt=85/15), and direct crystallization from heptane/AcOEt produced