2-bromo-1-(2,4-dichlorophenyl)ethanol

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: 102 mg of α-bromomethyl-2,4-dichlorobenzyl alcohol and the 82 mg of 2-(4-chlorobenzyloxymethyl)-3,4-dihydro-2H-pyran prepared above were then dissolved in 2 ml of diethyl ether, and one drop of phosphorus oxytrichloride was then added. The mixture was then allowed to react at room temperature for 4 days, after which it was treated and the product purified essentially as described in Example 34(a), to give 121 mg of trans-6-(4-chlorobenzyloxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran. to react at room temperature for 4 days after which it was treated the product purified essentially

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

Procedure: 102 mg of α-bromomethyl-2,4-dichlorobenzyl alcohol and the 82 mg of 2-(4-chlorobenzyloxymethyl)-3,4-dihydro-2H-pyran prepared above were then dissolved in 2 ml of diethyl ether, and one drop of phosphorus oxytrichloride was then added. The mixture was then allowed to react at room temperature for 4 days, after which it was treated and the product purified essentially as described in Example 34(a), to give 121 mg of trans-6-(4-chlorobenzyloxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran. to react at room temperature for 4 days after which it was treated the product purified essentially

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

Procedure: 389 mg of α-bromomethyl-2,4-dichlorobenzyl alcohol and 300 mg of 2-(4-fluorophenoxymethyl)-3,4-dihydro-2H-pyran, prepared as described above, were dissolved in 10 ml of diethyl ether. A catalytic amount (2 drops) of phosphorus oxytrichloride was added to the resulting solution and the mixture allowed to react at room temperature for 4 days, after which it was treated and the product purified essentially as described in Example 34(a), to give 214 mg of the isomer of lesser polarity of trans-6-(4-fluorophenoxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran, 211 mg of the isomer of greater polarity and 143 mg of a mixture of these isomers. to react at room temperature for 4 days after which it was treated the product purified essentially

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

Procedure: 389 mg of α-bromomethyl-2,4-dichlorobenzyl alcohol and 300 mg of 2-(4-fluorophenoxymethyl)-3,4-dihydro-2H-pyran, prepared as described above, were dissolved in 10 ml of diethyl ether. A catalytic amount (2 drops) of phosphorus oxytrichloride was added to the resulting solution and the mixture allowed to react at room temperature for 4 days, after which it was treated and the product purified essentially as described in Example 34(a), to give 214 mg of the isomer of lesser polarity of trans-6-(4-fluorophenoxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran, 211 mg of the isomer of greater polarity and 143 mg of a mixture of these isomers. to react at room temperature for 4 days after which it was treated the product purified essentially

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

Procedure: To 10 ml of an ethereal solution of 425 mg of α-bromomethyl-2,4-dichlorobenzyl alcohol and 340 mg of 2-(2,4-dichlorophenoxymethyl)-3,4-dihydro-2H-pyran was added a catalytic amount (2 drops) of phosphorus oxytrichloride, and the mixture was stirred at room temperature for 4 days. 3 drops of triethylamine were then added and the solvent was evaporated off under reduced pressure. The residue was purified by column chromatography through silica gel eluted with a 40:2:1 by volume mixture of hexane, benzene and ethyl acetate, to give 681 mg of the isomer of lesser polarity of trans-6-(2,4-dichlorophenoxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran as colorless crystals melting at 104°-105° C. the solvent was evaporated off under reduced pressure The residue was purified by column chromatography through silica gel eluted with a 40:2:1 by volume mixture of hexane, benzene and ethyl acetate

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: 102 mg of α-bromomethyl-2,4-dichlorobenzyl alcohol and the 82 mg of 2-(4-chlorobenzyloxymethyl)-3,4-dihydro-2H-pyran prepared above were then dissolved in 2 ml of diethyl ether, and one drop of phosphorus oxytrichloride was then added. The mixture was then allowed to react at room temperature for 4 days, after which it was treated and the product purified essentially as described in Example 34(a), to give 121 mg of trans-6-(4-chlorobenzyloxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran. to react at room temperature for 4 days after which it was treated the product purified essentially

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

Procedure: 389 mg of α-bromomethyl-2,4-dichlorobenzyl alcohol and 300 mg of 2-(4-fluorophenoxymethyl)-3,4-dihydro-2H-pyran, prepared as described above, were dissolved in 10 ml of diethyl ether. A catalytic amount (2 drops) of phosphorus oxytrichloride was added to the resulting solution and the mixture allowed to react at room temperature for 4 days, after which it was treated and the product purified essentially as described in Example 34(a), to give 214 mg of the isomer of lesser polarity of trans-6-(4-fluorophenoxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran, 211 mg of the isomer of greater polarity and 143 mg of a mixture of these isomers. to react at room temperature for 4 days after which it was treated the product purified essentially

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

Procedure: To 10 ml of an ethereal solution of 425 mg of α-bromomethyl-2,4-dichlorobenzyl alcohol and 340 mg of 2-(2,4-dichlorophenoxymethyl)-3,4-dihydro-2H-pyran was added a catalytic amount (2 drops) of phosphorus oxytrichloride, and the mixture was stirred at room temperature for 4 days. 3 drops of triethylamine were then added and the solvent was evaporated off under reduced pressure. The residue was purified by column chromatography through silica gel eluted with a 40:2:1 by volume mixture of hexane, benzene and ethyl acetate, to give 681 mg of the isomer of lesser polarity of trans-6-(2,4-dichlorophenoxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran as colorless crystals melting at 104°-105° C. the solvent was evaporated off under reduced pressure The residue was purified by column chromatography through silica gel eluted with a 40:2:1 by volume mixture of hexane, benzene and ethyl acetate