4-fluoro-2-phenylmethoxyphenol

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

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

Procedure: To a stirred mixture of 2.5 parts of 4-fluoro-2-(phenylmethoxy)phenol, 2.3 parts of 1-bromo-3-chloropropane, 10 parts of water and 0.39 parts of tetrabutylammonium hydrogen sulfate was added dropwise a solution of 0.7 parts of sodium hydroxide in 5 parts of D at 60° C. (exothermic reaction: temperature rose to 70°). The whole was stirred for 2 hours at 70° C. After cooling, the product was extracted twice with methylbenzene. The combined extracts were dried, filtered and evaporated, yielding 3.4 parts (100%) of 1-(3-chloropropoxy)-4-fluoro-2-(phenylmethoxy)benzene as a residue (intermediate 78). (exothermic reaction: temperature rose to 70°) After cooling the product was extracted twice with methylbenzene The combined extracts were dried filtered evaporated

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

Procedure: A mixture of 11 parts of 1-[4-fluoro-2-(phenylmethoxy)phenyl]ethanone, 8.48 parts of 3-chlorobenzenecarboperoxoic acid and 260 parts of dichloromethane was stirred for 5 days at room temperature. The precipitate was filtered off and the filtrate was stirred in a saturate thiosulfurate solution for 15 minutes. The organic layer was separated and stirred in a saturate hydrogen carbonate solution for 15 minutes. The organic layer was separated, washed with water, dried, filtered and evaporated. The solid residue was stirred in 240 parts of methanol. 5.3 Parts of sodium methoxide were added portionwise. After complete addition, the whole was stirred for 1 hour at room temperature. After evaporation in vacuo at 50° C., the residue was stirred in water and acidified with a hydrochloric acid solution 3N. Trichloromethane was added, the organic layer was separated, washed twice with water, dried, filtered and evaporated, yielding 10 parts (93%) of 4-fluoro-2-(phenylmethoxy)phenol as a residue (intermediate 77). The precipitate was filtered off the filtrate was stirred in a saturate thiosulfurate solution for 15 minutes The organic layer was separated stirred in a saturate hydrogen carbonate solution for 15 minutes The organic layer was separated washed with water dried filtered evaporated The solid residue was stirred in 240 parts of methanol 5.3 Parts of sodium methoxide were added portionwise After complete addition the whole was stirred for 1 hour at room temperature After evaporation in vacuo at 50° C. the residue was stirred in water Trichloromethane was added the organic layer was separated washed twice with water dried filtered evaporated

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

Procedure: A mixture of 11 parts of 1-[4-fluoro-2-(phenylmethoxy)phenyl]ethanone, 8.48 parts of 3-chlorobenzenecarboperoxoic acid and 260 parts of dichloromethane was stirred for 5 days at room temperature. The precipitate was filtered off and the filtrate was stirred in a saturate thiosulfurate solution for 15 minutes. The organic layer was separated and stirred in a saturate hydrogen carbonate solution for 15 minutes. The organic layer was separated, washed with water, dried, filtered and evaporated. The solid residue was stirred in 240 parts of methanol. 5.3 Parts of sodium methoxide were added portionwise. After complete addition, the whole was stirred for 1 hour at room temperature. After evaporation in vacuo at 50° C., the residue was stirred in water and acidified with a hydrochloric acid solution 3N. Trichloromethane was added, the organic layer was separated, washed twice with water, dried, filtered and evaporated, yielding 10 parts (93%) of 4-fluoro-2-(phenylmethoxy)phenol as a residue (intermediate 77). The precipitate was filtered off the filtrate was stirred in a saturate thiosulfurate solution for 15 minutes The organic layer was separated stirred in a saturate hydrogen carbonate solution for 15 minutes The organic layer was separated washed with water dried filtered evaporated The solid residue was stirred in 240 parts of methanol 5.3 Parts of sodium methoxide were added portionwise After complete addition the whole was stirred for 1 hour at room temperature After evaporation in vacuo at 50° C. the residue was stirred in water Trichloromethane was added the organic layer was separated washed twice with water dried filtered evaporated

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

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

Procedure: To a stirred mixture of 2.5 parts of 4-fluoro-2-(phenylmethoxy)phenol, 2.3 parts of 1-bromo-3-chloropropane, 10 parts of water and 0.39 parts of tetrabutylammonium hydrogen sulfate was added dropwise a solution of 0.7 parts of sodium hydroxide in 5 parts of D at 60° C. (exothermic reaction: temperature rose to 70°). The whole was stirred for 2 hours at 70° C. After cooling, the product was extracted twice with methylbenzene. The combined extracts were dried, filtered and evaporated, yielding 3.4 parts (100%) of 1-(3-chloropropoxy)-4-fluoro-2-(phenylmethoxy)benzene as a residue (intermediate 78). (exothermic reaction: temperature rose to 70°) After cooling the product was extracted twice with methylbenzene The combined extracts were dried filtered evaporated

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

Procedure: To a stirred mixture of 2.5 parts of 4-fluoro-2-(phenylmethoxy)phenol, 2.3 parts of 1-bromo-3-chloropropane, 10 parts of water and 0.39 parts of tetrabutylammonium hydrogen sulfate was added dropwise a solution of 0.7 parts of sodium hydroxide in 5 parts of D at 60° C. (exothermic reaction: temperature rose to 70°). The whole was stirred for 2 hours at 70° C. After cooling, the product was extracted twice with methylbenzene. The combined extracts were dried, filtered and evaporated, yielding 3.4 parts (100%) of 1-(3-chloropropoxy)-4-fluoro-2-(phenylmethoxy)benzene as a residue (intermediate 78). (exothermic reaction: temperature rose to 70°) After cooling the product was extracted twice with methylbenzene The combined extracts were dried filtered evaporated

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

Procedure: A mixture of 11 parts of 1-[4-fluoro-2-(phenylmethoxy)phenyl]ethanone, 8.48 parts of 3-chlorobenzenecarboperoxoic acid and 260 parts of dichloromethane was stirred for 5 days at room temperature. The precipitate was filtered off and the filtrate was stirred in a saturate thiosulfate solution for 15 minutes. The organic layer was separated and stirred in a saturate hydrogen carbonate solution for 15 minutes. The organic layer was separated, washed with water, dried, filtered and evaporated. The solid residue was stirred in 240 parts of methanol. 5.3 Parts of sodium methoxide were added portionwise. After complete addition, the whole was stirred for 1 hour at room temperature. After evaporation in vacuo at 50° C., the residue was stirred in water and acidified with a hydrochloric acid solution 3N. Trichloromethane was added, the organic layer was separated, washed twice with water, dried, filtered and evaporated, yielding 10 parts (93%) of 4-fluoro-2-(phenylmethoxy)phenol as a residue (intermediate 77). The precipitate was filtered off the filtrate was stirred in a saturate thiosulfate solution for 15 minutes The organic layer was separated stirred in a saturate hydrogen carbonate solution for 15 minutes The organic layer was separated washed with water dried filtered evaporated The solid residue was stirred in 240 parts of methanol 5.3 Parts of sodium methoxide were added portionwise After complete addition the whole was stirred for 1 hour at room temperature After evaporation in vacuo at 50° C. the residue was stirred in water Trichloromethane was added the organic layer was separated washed twice with water dried filtered evaporated

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

Procedure: To a stirred mixture of 2.5 parts of 4-fluoro-2-(phenylmethoxy)phenol, 2.3 parts of 1-bromo-3-chloropropane, 10 parts of water and 0.39 parts of tetrabutylammonium hydrogen sulfate was added dropwise a solution of 0.7 parts of sodium hydroxide in 5 parts of D at 60° C. (exothermic reaction: temperature rose to 70°). The whole was stirred for 2 hours at 70° C. After cooling, the product was extracted twice with methylbenzene. The combined extracts were dried, filtered and evaporated, yielding 3.4 parts (100%) of 1-(3-chloropropoxy)-4-fluoro-2-(phenylmethoxy)benzene as a residue (intermediate 78). (exothermic reaction: temperature rose to 70°) After cooling the product was extracted twice with methylbenzene The combined extracts were dried filtered evaporated

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

Procedure: A mixture of 11 parts of 1-[4-fluoro-2-(phenylmethoxy)phenyl]ethanone, 8.48 parts of 3-chlorobenzenecarboperoxoic acid and 260 parts of dichloromethane was stirred for 5 days at room temperature. The precipitate was filtered off and the filtrate was stirred in a saturate thiosulfurate solution for 15 minutes. The organic layer was separated and stirred in a saturate hydrogen carbonate solution for 15 minutes. The organic layer was separated, washed with water, dried, filtered and evaporated. The solid residue was stirred in 240 parts of methanol. 5.3 Parts of sodium methoxide were added portionwise. After complete addition, the whole was stirred for 1 hour at room temperature. After evaporation in vacuo at 50° C., the residue was stirred in water and acidified with a hydrochloric acid solution 3N. Trichloromethane was added, the organic layer was separated, washed twice with water, dried, filtered and evaporated, yielding 10 parts (93%) of 4-fluoro-2-(phenylmethoxy)phenol as a residue (intermediate 77). The precipitate was filtered off the filtrate was stirred in a saturate thiosulfurate solution for 15 minutes The organic layer was separated stirred in a saturate hydrogen carbonate solution for 15 minutes The organic layer was separated washed with water dried filtered evaporated The solid residue was stirred in 240 parts of methanol 5.3 Parts of sodium methoxide were added portionwise After complete addition the whole was stirred for 1 hour at room temperature After evaporation in vacuo at 50° C. the residue was stirred in water Trichloromethane was added the organic layer was separated washed twice with water dried filtered evaporated