Pentabromophenol

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: Pentabromophenol (1.0 g, 2.05 mmol) and AlCl3 (4.1 g, 30.75 mmol) were mixed in toluene (20 mL) and heated at reflux temperature under a nitrogen atmosphere overnight. The reaction mixture was cooled, cautiously added to ice, filtered and the filtrate was extracted with EtOAc (3×50 mL). The organics were dried (Na2SO4) and concentrated in vacuo. The residue obtained was purified by chromatography on silica gel with EtOAc:heptane (1:4, v/v) as eluent to afford the title compound as a white solid (230 mg, 0.91 mmol, 45%). heated at reflux temperature under a nitrogen atmosphere overnight The reaction mixture was cooled cautiously added to ice filtered the filtrate was extracted with EtOAc (3×50 mL) The organics were dried (Na2SO4) concentrated in vacuo The residue obtained was purified by chromatography on silica gel with EtOAc:heptane (1:4, v/v) as eluent

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

Procedure: Pentabromophenol (1.0 g, 2.05 mmol) and AlCl3 (4.1 g, 30.75 mmol) were mixed in toluene (20 mL) and heated at reflux temperature under a nitrogen atmosphere overnight. The reaction mixture was cooled, cautiously added to ice, filtered and the filtrate was extracted with EtOAc (3×50 mL). The organics were dried (Na2SO4) and concentrated in vacuo. The residue obtained was purified by chromatography on silica gel with EtOAc:heptane (1:4, v/v) as eluent to afford the title compound as a white solid (230 mg, 0.91 mmol, 45%). heated at reflux temperature under a nitrogen atmosphere overnight The reaction mixture was cooled cautiously added to ice filtered the filtrate was extracted with EtOAc (3×50 mL) The organics were dried (Na2SO4) concentrated in vacuo The residue obtained was purified by chromatography on silica gel with EtOAc:heptane (1:4, v/v) as eluent

Conditions: temp:143.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of pentabromophenol (100 g., 0.2 moles), potassium carbonate (30 g., 0.22 moles), potassium iodide (0.5 g.), dimethyl formamide (180 ml.) and 3,3-bischloromethyl oxetane (15.5 g., 0.1 moles) was stirred in a nitrogen atmosphere and heated to 143° C. for 5 hours. The partially cooled reaction mixture was poured into 1 liter of water. The resulting solid 3,3-bis[pentabromophenoxymethyl]oxetane was collected by filtration and washed on the funnel with water and with ethanol. The yield was 93 g. A small sample was recrystallized from a large volume of dioxane. The recrystallized material melted at 281°-284° C. The partially cooled reaction mixture The resulting solid 3,3-bis[pentabromophenoxymethyl]oxetane was collected by filtration washed on the funnel with water and with ethanol A small sample was recrystallized from a large volume of dioxane

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

Procedure: To 31.5 g. (0.07 moles) of 3-[2,4,6-tribromophenoxymethyl]-3-[chloromethyl]oxetane was added pentabromophenol (36 g., 0.074 moles), potassium carbonate (10 g., 0.077 moles), potassium iodide (0.5 g.) and dimethyl formamide (75 ml.). The reactants were stirred in a nitrogen atmosphere and heated to 140°-148° C. for 21/2 hours. The cooled reaction mixture was diluted with 500 ml. of water. The resulting solid 3-[2,4,6-tribromophenoxymethyl]-3-[pentabromophenoxymethyl]oxetane was collected by filtration and washed on the funnel with water and with ethanol. The yield was 48 g. (76%). A small sample recrystallized from dioxane (6 ml./g.) melted at 202°-204° C. heated to 140°-148° C. for 21/2 hours The cooled reaction mixture was diluted with 500 ml The resulting solid 3-[2,4,6-tribromophenoxymethyl]-3-[pentabromophenoxymethyl]oxetane was collected by filtration washed on the funnel with water and with ethanol A small sample recrystallized from dioxane (6 ml./g.) melted at 202°-204° C.

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

Procedure: To 31.5 g. (0.07 moles) of 3-[2,4,6-tribromophenoxymethyl]-3-[chloromethyl]oxetane was added pentabromophenol (36 g., 0.074 moles), potassium carbonate (10 g., 0.077 moles), potassium iodide (0.5 g.) and dimethyl formamide (75 ml.). The reactants were stirred in a nitrogen atmosphere and heated to 140°-148° C. for 21/2 hours. The cooled reaction mixture was diluted with 500 ml. of water. The resulting solid 3-[2,4,6-tribromophenoxymethyl]-3-[pentabromophenoxymethyl]oxetane was collected by filtration and washed on the funnel with water and with ethanol. The yield was 48 g. (76%). A small sample recrystallized from dioxane (6 ml./g.) melted at 202°-204° C. heated to 140°-148° C. for 21/2 hours The cooled reaction mixture was diluted with 500 ml The resulting solid 3-[2,4,6-tribromophenoxymethyl]-3-[pentabromophenoxymethyl]oxetane was collected by filtration washed on the funnel with water and with ethanol A small sample recrystallized from dioxane (6 ml./g.) melted at 202°-204° C.

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

Procedure: 600 ml. of methyl glycol, 97.75 g (0.2 mole) of pentabromophenol, 8 g (0.2 mole) of sodium hydroxide in 8 ml of water, and 28.12 g (0.2 mole) of 1-chloromethyl-4-methyl-benzene were reacted in the manner previously described. At 65° C. the reaction perceptibly commenced. The ether crystallized in long needles during the refluxing of the mixture. Yield: 96 g (81%), M.P. 194° C. 10 g recrystallized from 300 ml of methoxyethyl chloride had a melting point of 200°-202° C. At 65° C. the reaction The ether crystallized in long needles during the refluxing of the mixture 10 g recrystallized from 300 ml of methoxyethyl chloride

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

Procedure: Pentabromophenol (1.0 g, 2.05 mmol) and AlCl3 (4.1 g, 30.75 mmol) were mixed in toluene (20 mL) and heated at reflux temperature under a nitrogen atmosphere overnight. The reaction mixture was cooled, cautiously added to ice, filtered and the filtrate was extracted with EtOAc (3×50 mL). The organics were dried (Na2SO4) and concentrated in vacuo. The residue obtained was purified by chromatography on silica gel with EtOAc:heptane (1:4, v/v) as eluent to afford the title compound as a white solid (230 mg, 0.91 mmol, 45%). heated at reflux temperature under a nitrogen atmosphere overnight The reaction mixture was cooled cautiously added to ice filtered the filtrate was extracted with EtOAc (3×50 mL) The organics were dried (Na2SO4) concentrated in vacuo The residue obtained was purified by chromatography on silica gel with EtOAc:heptane (1:4, v/v) as eluent

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

Procedure: In a two-liter flask, 5.6 of potassium hydroxide was dissolved at 75° C in 800 ml of methyl glycol; then 48.9 g (= 0.1 mole) of pentabromphenol was stirred in. To this phenolate solution, at 75° C, 64.15 g was added of the o-chloromethylbenzoic acid pentabromophenyl ester, prepared as in Example 9a, and the mixture was heated with stirring to ebullition. It was refluxed for an hour, then cooled, and the solids were isolated and worked up as described in the preceding examples. the mixture was heated It was refluxed for an hour cooled the solids were isolated

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

Procedure: In a 500-ml three-necked flask, 4 g (= 0.1 mole) of sodium hydroxide was dissolved at 60° C in 270 ml of methyl glycol, and 48.9 g of pentabromophenol was stirred in for the preparation of a phenolate solution, as in Example 8c. At 30° to 34° C, 18.9 g (- 0.1 mole) of o-chloromethylbenzoyl chloride was added drop by drop, with stirring, over a period of about 40 minutes, whereupon a white, crystalline preciptate settled out, which after 1 hour was suction filtered. After the product had been stirred up in water, suction filtered, washed and dried, 58 g (= 90.5%) of o-chloromethylbenzoic acid pentabromophenyl ester was obtained, which melted at 201°-205° C. which after 1 hour was suction filtered After the product had been stirred up in water suction filtered washed dried

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

Procedure: Tris-(pentabromophenoxy)-s-triazine was prepared from pentabromophenol and cyanuric chloride using the process described in Example 1, above. The compound was found to have a melting point of 320°-325°C.