6-bromo-2-methoxynaphthalene-1-carbaldehyde

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The compound is prepared by the reaction of 6-bromo-2-methoxy-1-naphthaldehyde (2 g, 7.55 mmol, 1 eq) with 3-methoxyphenylboric acid (1.3 g, 8.30 mmol, 1.1 eq) according to method A. Purification by column chromatography with hexane/ethyl acetate 1/1 as the eluent yielded the desired compound in a yield of 86%, 1.9 g. Purification by column chromatography with hexane/ethyl acetate 1/1 as the eluent

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

Procedure: 9.7 ml of TiCl4 (2.1 eq) and 4.2 ml of dichloromethyl methyl ether (1.1 eq) are dissolved in 20 ml of dichloromethane at 0° C. A solution of 10 g of 2-bromo-6-methoxynapthalene (1 eq) is added dropwise in such a way that the temperature does not exceed 5° C. The reaction mixture is stirred at RT over night, followed by the addition of 300 ml of 1% HCl. The organic and aqueous phases are separated, and the aqueous phase is extracted with dichloromethane. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness on a rotary evaporator to obtain the desired product in quantitative yield (11 g). does not exceed 5° C The organic and aqueous phases are separated the aqueous phase is extracted with dichloromethane The combined organic phases are washed with saturated sodium chloride solution dried over magnesium sulfate evaporated to dryness on a rotary evaporator

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The compound is prepared by the reaction of 6-bromo-2-methoxy-1-naphthaldehyde (2 g, 7.55 mmol, 1 eq) with 3-methoxyphenylboric acid (1.3 g, 8.30 mmol, 1.1 eq) according to method A. Purification by column chromatography with hexane/ethyl acetate 1/1 as the eluent yielded the desired compound in a yield of 86%, 1.9 g. Purification by column chromatography with hexane/ethyl acetate 1/1 as the eluent

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

Procedure: 9.7 ml of TiCl4 (2.1 eq) and 4.2 ml of dichloromethyl methyl ether (1.1 eq) are dissolved in 20 ml of dichloromethane at 0° C. A solution of 10 g of 2-bromo-6-methoxynapthalene (1 eq) is added dropwise in such a way that the temperature does not exceed 5° C. The reaction mixture is stirred at RT over night, followed by the addition of 300 ml of 1% HCl. The organic and aqueous phases are separated, and the aqueous phase is extracted with dichloromethane. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness on a rotary evaporator to obtain the desired product in quantitative yield (11 g). does not exceed 5° C The organic and aqueous phases are separated the aqueous phase is extracted with dichloromethane The combined organic phases are washed with saturated sodium chloride solution dried over magnesium sulfate evaporated to dryness on a rotary evaporator