2-(4-bromophenoxy)-N,N-dimethylethanamine

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

Procedure: 4-Bromophenol (10.0 g, 57.8 mmol) and 2-dimethylaminoethyl chloride hydrochloride (8.33 g, 57.8 mmol) were dissolved in DMF (200 ml), and potassium carbonate (24.0 g, 173 mmol) and sodium iodide (0.87 g, 5.78 mmol) were added under ice-cooling. The mixture was stirred for 13 hr at room temperature and at 70° C. for 3 hr. Water (400 ml) was added to the reaction mixture and the mixture was extracted with chloroform (2×200 ml). The organic layer was washed successively with water (2×200 ml) and saturated brine (200 ml), dried over anhydrous magnesium sulfate and concentrated. The obtained residue was dissolved in 1N hydrochloric acid (100 ml) and washed with ethyl acetate (2×200 ml). Sodium hydroxide (4 g) was added to the aqueous layer to make the layer alkaline, and the mixture was extracted with chloroform (2×200 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated. Hexane was added to the obtained residue and insoluble matter was filtered off. The mother liquor was concentrated to give the title compound (5.25 g, 37%) as a transparent oil. cooling the mixture was extracted with chloroform (2×200 ml) The organic layer was washed successively with water (2×200 ml) and saturated brine (200 ml) dried over anhydrous magnesium sulfate concentrated The obtained residue was dissolved in 1N hydrochloric acid (100 ml) washed with ethyl acetate (2×200 ml) Sodium hydroxide (4 g) was added to the aqueous layer the mixture was extracted with chloroform (2×200 ml) The organic layer was dried over anhydrous magnesium sulfate concentrated Hexane was added to the obtained residue and insoluble matter was filtered off The mother liquor was concentrated

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

Procedure: To a Grignard reactant prepared from 2.2 g. of magnesium turnings and 23.4 g. of 4-[2-(dimethylamino)-ethoxy]-bromobenzene in 100 ml. of dry tetrahydrofurane a solution of 10 g. of m-chloro-propiophenone in 30 ml. of tetrahydrofurane is added dropwise, at 20° C. The reaction mixture is stirred at room temperature for another two hours, cooled, and filtered onto a 20% aqueous ammonium chloride solution. Tetrahydrofurane is distilled off in vacuo. The residue is extracted with ether, the ethereal phase is washed with water, dried over anhydrous magnesium sulfate, filtered, and ether is distilled off. Crystallization of the residue from a mixture of n-hexane and ethyl acetate yields 14.2 g. of the named compound, melting at 108° to 109° C. cooled filtered onto a 20% aqueous ammonium chloride solution Tetrahydrofurane is distilled off in vacuo The residue is extracted with ether the ethereal phase is washed with water dried over anhydrous magnesium sulfate filtered ether is distilled off Crystallization of the residue from a mixture of n-hexane and ethyl acetate yields 14.2 g

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

Procedure: 2-cyclopentyl-1-[p-(N,N-dimethyl-2-aminoethoxy)phenyl]-1-(p-hydroxyphenyl)-1-butanol, which was prepared from α-cyclopentyl-p-hydroxybutyrophenone and p-(N,N-dimethyl-2-aminoethoxy) bromobenzene according to the procedure of example 3, was dehydrated in ethanol in the presence of hydrochloric acid. The product was recrystallized from n-hexane, mp. 112°-120° C. and was found to be an 1:1 mixture of E- and Z-isomers. The product was recrystallized from n-hexane, mp. 112°-120° C. an 1:1 mixture of E- and Z-isomers

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

Procedure: 2-cyclopentyl-1-[p-(N,N-dimethyl-2-aminoethoxy)phenyl]-1-(p-hydroxyphenyl)-1-butanol, which was prepared from α-cyclopentyl-p-hydroxybutyrophenone and p-(N,N-dimethyl-2-aminoethoxy) bromobenzene according to the procedure of example 3, was dehydrated in ethanol in the presence of hydrochloric acid. The product was recrystallized from n-hexane, mp. 112°-120° C. and was found to be an 1:1 mixture of E- and Z-isomers. The product was recrystallized from n-hexane, mp. 112°-120° C. an 1:1 mixture of E- and Z-isomers

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

Procedure: Prepared according to the procedure analogous to that described above for [2-(4-Bromo-phenoxy)-ethyl]-diethyl-amine, except using (2-chloro-ethyl)-dimethylamine hydrochloride. Prepared

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

Procedure: Prepared according to the procedure analogous to that described above for [2-(4-Bromo-phenoxy)-ethyl]-diethyl-amine, except using (2-chloro-ethyl)-dimethylamine hydrochloride. Prepared

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

Procedure: Prepared from [2-(4-bromo-phenoxy)-ethyl]-dimethyl-amine according to general Method I for borylation described above for preparation of 4,4,5,5-tetramethyl-2-(2-methyl-4-phenoxy-phenyl)-[1,3,2]dioxaborolane.

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

Procedure: 4-Bromophenol (10.0 g, 57.8 mmol) and 2-dimethylaminoethyl chloride hydrochloride (8.33 g, 57.8 mmol) were dissolved in DMF (200 ml), and potassium carbonate (24.0 g, 173 mmol) and sodium iodide (0.87 g, 5.78 mmol) were added under ice-cooling. The mixture was stirred for 13 hr at room temperature and at 70° C. for 3 hr. Water (400 ml) was added to the reaction mixture and the mixture was extracted with chloroform (2×200 ml). The organic layer was washed successively with water (2×200 ml) and saturated brine (200 ml), dried over anhydrous magnesium sulfate and concentrated. The obtained residue was dissolved in 1N hydrochloric acid (100 ml) and washed with ethyl acetate (2×200 ml). Sodium hydroxide (4 g) was added to the aqueous layer to make the layer alkaline, and the mixture was extracted with chloroform (2×200 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated. Hexane was added to the obtained residue and insoluble matter was filtered off. The mother liquor was concentrated to give the title compound (5.25 g, 37%) as a transparent oil. cooling the mixture was extracted with chloroform (2×200 ml) The organic layer was washed successively with water (2×200 ml) and saturated brine (200 ml) dried over anhydrous magnesium sulfate concentrated The obtained residue was dissolved in 1N hydrochloric acid (100 ml) washed with ethyl acetate (2×200 ml) Sodium hydroxide (4 g) was added to the aqueous layer the mixture was extracted with chloroform (2×200 ml) The organic layer was dried over anhydrous magnesium sulfate concentrated Hexane was added to the obtained residue and insoluble matter was filtered off The mother liquor was concentrated

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

Procedure: 4-Bromophenol (10.0 g, 57.8 mmol) and 2-dimethylaminoethyl chloride hydrochloride (8.33 g, 57.8 mmol) were dissolved in DMF (200 ml), and potassium carbonate (24.0 g, 173 mmol) and sodium iodide (0.87 g, 5.78 mmol) were added under ice-cooling. The mixture was stirred for 13 hr at room temperature and at 70° C. for 3 hr. Water (400 ml) was added to the reaction mixture and the mixture was extracted with chloroform (2×200 ml). The organic layer was washed successively with water (2×200 ml) and saturated brine (200 ml), dried over anhydrous magnesium sulfate and concentrated. The obtained residue was dissolved in 1N hydrochloric acid (100 ml) and washed with ethyl acetate (2×200 ml). Sodium hydroxide (4 g) was added to the aqueous layer to make the layer alkaline, and the mixture was extracted with chloroform (2×200 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated. Hexane was added to the obtained residue and insoluble matter was filtered off. The mother liquor was concentrated to give the title compound (5.25 g, 37%) as a transparent oil. cooling the mixture was extracted with chloroform (2×200 ml) The organic layer was washed successively with water (2×200 ml) and saturated brine (200 ml) dried over anhydrous magnesium sulfate concentrated The obtained residue was dissolved in 1N hydrochloric acid (100 ml) washed with ethyl acetate (2×200 ml) Sodium hydroxide (4 g) was added to the aqueous layer the mixture was extracted with chloroform (2×200 ml) The organic layer was dried over anhydrous magnesium sulfate concentrated Hexane was added to the obtained residue and insoluble matter was filtered off The mother liquor was concentrated