1-bromo-2-methoxynaphthalene

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

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

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

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

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

Procedure: To a flask charged with 1-bromo-2-methoxynaphthalene (20.0 g, 84.4 mmol), phenylboronic acid (11.3 g, 92.8 mmol), palladium acetate (0.10 g, 0.46 mmol), triphenylphosphine (0.85 g, 2.78 mmol) and potassium phosphate (40.9 g, 177.9 mmol), added was mixture of water (60 mL) and dimethoxyethane (120 mL), and the resultant mixture was heated under reflux for 6 hours. After cooling the mixture to ambient temperature, aqueous ammonium chloride solution (150 mL) and diethyl ether (200 mL) were injected thereto. The organic layer was isolated, and the residue was extracted with diethyl ether. The combined organic layer was dried over magnesium sulfate and evaporated to remove the volatile substances. Purification via silica gel column chromatography (n-hexane) gave 2-methoxy-1-phenylnaphthalene (13.0 g, yield: 66%) as colorless liquid. added under reflux for 6 hours The organic layer was isolated the residue was extracted with diethyl ether The combined organic layer was dried over magnesium sulfate evaporated to remove the volatile substances Purification via silica gel column chromatography (n-hexane)

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

Procedure: Compared with the preparation of analogues of the compound II-A, ie 1-(6-methoxy-2-naphthyl)-1-propanone (II, X=H) and 1-(5-bromo-6-methoxy-2-naphthyl)-1-propanone (II, X=Br) by a Friedel-Crafts reaction between propionyl chloride and, respectively, 2-methoxy-naphthalene and 1-bromo-2-methoxy-naphthalene, the following advantages are obtained: Compared with the preparation of analogues of the compound II-A

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

Procedure: 48 Grams of naphthalene and 16.7 g of anhydrous aluminum chloride are added to the solution of 2-acetyl-5-bromo-6-methoxynaphthalene obtained as in example 1a), while keeping the temperature at -10° C. The reaction mixture is kept under stirring for 2 hours at 0° C. and for 20 hours at room temperature and then it is worked as in example 1 obtaining 38.8 g of product with a yield equal to 79.2% calculated on the basis of the starting material 1-bromo-2-methoxynaphthalene. obtained as in example 1a), at -10° C

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

Procedure: 80 Ml of anisole and 18 g of anhydrous aluminum chloride are added to the solution of 2-acetyl-5-bromo-6-methoxynaphthalene obtained as in example 1a), while keeping the temperature at -10° C. The reaction mixture is kept for 24 hours under stirring at room temperature and then it is worked as in example 1 obtaining 38.5 g of product with a yield equal to 78.5% calculated on the basis of the starting material 1-bromo-2-methoxynaphthalene. obtained as in example 1a), at -10° C

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

Procedure: 80 Ml of anisole and 18 g of anhydrous aluminum chloride are added to the solution of 2-acetyl-5-bromo-6-methoxynaphthalene obtained as in example 1a), while keeping the temperature at -10° C. The reaction mixture is kept for 24 hours under stirring at room temperature and then it is worked as in example 1 obtaining 38.5 g of product with a yield equal to 78.5% calculated on the basis of the starting material 1-bromo-2-methoxynaphthalene. obtained as in example 1a), at -10° C

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

Procedure: 42 Ml of β-naphthol and 16.2 g of anhydrous aluminum chloride are added to the solution of 2-acetyl-5-bromo-6-methoxynaphthalene obtained as in example 1a), while keeping the temperature at -10° C. The reaction mixture is kept for 48 hours under stirring at room temperature and then it is worked as in example 1 with the only difference that the product is crystallized by isopropyl alcohol. 19 Grams of product are obtained with a yield equal to 38.7% calculated on the basis of the starting material 1-bromo-2-methoxynaphthalene. obtained as in example 1a), at -10° C is crystallized by isopropyl alcohol 19 Grams of product are obtained with a yield equal to 38.7%

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

Procedure: 57 Ml of tert-butylbenzene and 8.2 g of anhydrous aluminum chloride are added to the solution of 2-acetyl-5-bromo-6-methoxynaphthalene obtained as in example 1a), while keeping the temperature at -10° C. The reaction mixture is kept for 16 hours under stirring at room temperature and then it is worked as in example 1 obtaining 41.8 g of product with a yield equal to 85.3% calculated on the basis of the starting material 1-bromo-2-methoxynaphthalene. obtained as in example 1a), at -10° C

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

Procedure: 57 Ml of tert-butylbenzene and 8.2 g of anhydrous aluminum chloride are added to the solution of 2-acetyl-5-bromo-6-methoxynaphthalene obtained as in example 1a), while keeping the temperature at -10° C. The reaction mixture is kept for 16 hours under stirring at room temperature and then it is worked as in example 1 obtaining 41.8 g of product with a yield equal to 85.3% calculated on the basis of the starting material 1-bromo-2-methoxynaphthalene. obtained as in example 1a), at -10° C