4,6-DICHLORORESORCINOL

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: 4,6-dichlororesorcinol (3.80 g, 21 mmol), allyl bromide (1.82 mL, 21 mmol) and potassium carbonate (2.24 g, 21 mmol) were combined in DMF and stirred at room temperature for 18 hours. The DMF was removed in vacuo and the residue acidified with 2M hydrochloric acid (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic solution was dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with pentane:ethyl acetate 9:1 to 4:1 to afford the title compound as a yellow oil in 27% yield, 1.24 g. The DMF was removed in vacuo extracted with ethyl acetate (2×50 mL) The combined organic solution was dried over magnesium sulphate concentrated in vacuo The residue was purified by column chromatography on silica gel eluting with pentane:ethyl acetate 9:1 to 4:1

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

Procedure: 4,6-dichlororesorcinol (3.80 g, 21 mmol), allyl bromide (1.82 mL, 21 mmol) and potassium carbonate (2.24 g, 21 mmol) were combined in DMF and stirred at room temperature for 18 hours. The DMF was removed in vacuo and the residue acidified with 2M hydrochloric acid (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic solution was dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with pentane:ethyl acetate 9:1 to 4:1 to afford the title compound as a yellow oil in 27% yield, 1.24 g. The DMF was removed in vacuo extracted with ethyl acetate (2×50 mL) The combined organic solution was dried over magnesium sulphate concentrated in vacuo The residue was purified by column chromatography on silica gel eluting with pentane:ethyl acetate 9:1 to 4:1

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

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

Procedure: 4,6-dichlororesorcinol (3.80 g, 21 mmol), allyl bromide (1.82 mL, 21 mmol) and potassium carbonate (2.24 g, 21 mmol) were combined in DMF and stirred at room temperature for 18 hours. The DMF was removed in vacuo and the residue acidified with 2M hydrochloric acid (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic solution was dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with pentane:ethyl acetate 9:1 to 4:1 to afford the title compound as a yellow oil in 27% yield, 1.24 g. The DMF was removed in vacuo extracted with ethyl acetate (2×50 mL) The combined organic solution was dried over magnesium sulphate concentrated in vacuo The residue was purified by column chromatography on silica gel eluting with pentane:ethyl acetate 9:1 to 4:1

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

Procedure: 4,6-dichlororesorcinol (3.80 g, 21 mmol), allyl bromide (1.82 mL, 21 mmol) and potassium carbonate (2.24 g, 21 mmol) were combined in DMF and stirred at room temperature for 18 hours. The DMF was removed in vacuo and the residue acidified with 2M hydrochloric acid (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic solution was dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with pentane:ethyl acetate 9:1 to 4:1 to afford the title compound as a yellow oil in 27% yield, 1.24 g. The DMF was removed in vacuo extracted with ethyl acetate (2×50 mL) The combined organic solution was dried over magnesium sulphate concentrated in vacuo The residue was purified by column chromatography on silica gel eluting with pentane:ethyl acetate 9:1 to 4:1

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4,6-Dichlororesorcinol (25 g, 0.14 mol), epichlorohydrin (129 g, 1.4 mol) and isopropyl alcohol (100 ml) were added to a three-neck round bottom flask equipped with a reflux condenser and a mechanic stirrer. A solution of sodium hydroxide (12 g) in water (14 g) was placed in an addition funnel. The flask contents were raised to 75° C. The sodium hydroxide solution was added over 6 hours while the reaction was held at 75° C. After the slow addition the reaction was held at 83° C. for an additional 2 hours. The material was filtered and the solvent was removed. The product was then redissolved in toluene and washed with deionized water. The product in toluene was collected after one wash and passed through a silica gel column. The product was collected by removal of the solvent. Yield 50%, mp 78° C., 1H NMR (CDCl3): δppm 2.7-2.9 (4H), 3.3 (2H), 3.9-4.3 (4H), 6.7-7.3 (2H). equipped with a reflux condenser and a mechanic stirrer was held at 75° C After the slow addition the reaction The material was filtered the solvent was removed The product was then redissolved in toluene washed with deionized water The product in toluene was collected after one wash The product was collected by removal of the solvent

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4,6-dichlororesorcinol (2 g), potassium carbonate (1.54 g) and methyl bromoacetate (1.71 g) in DMF (10 ml) was heated at 80° C. for 24 h. The resulting mixture was cooled and water (200 ml) added. Solid (bis-alkylated product) was filtered off, then the aqueous was acidified with aq. HCl, which was extracted with ether and the organics were dried and concentrated in vacuo. Purification by RPHPLC (Xterra, gradient 95-5%, ammonia (0.2% aq.) in acetonitrile) gave the subtitle compound (0.65 g) as a solid. The resulting mixture was cooled Solid (bis-alkylated product) was filtered off was extracted with ether the organics were dried concentrated in vacuo Purification by RPHPLC (Xterra, gradient 95-5%, ammonia (0.2% aq.) in acetonitrile)

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

Procedure: 4,6-dichlororesorcinol (3.80 g, 21 mmol), allyl bromide (1.82 mL, 21 mmol) and potassium carbonate (2.24 g, 21 mmol) were combined in DMF and stirred at room temperature for 18 hours. The DMF was removed in vacuo and the residue acidified with 2M hydrochloric acid (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic solution was dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with pentane:ethyl acetate 9:1 to 4:1 to afford the title compound as a yellow oil in 27% yield, 1.24 g. The DMF was removed in vacuo extracted with ethyl acetate (2×50 mL) The combined organic solution was dried over magnesium sulphate concentrated in vacuo The residue was purified by column chromatography on silica gel eluting with pentane:ethyl acetate 9:1 to 4:1

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

Procedure: 4,6-dichlororesorcinol (3.80 g, 21 mmol), allyl bromide (1.82 mL, 21 mmol) and potassium carbonate (2.24 g, 21 mmol) were combined in DMF and stirred at room temperature for 18 hours. The DMF was removed in vacuo and the residue acidified with 2M hydrochloric acid (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic solution was dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with pentane:ethyl acetate 9:1 to 4:1 to afford the title compound as a yellow oil in 27% yield, 1.24 g. The DMF was removed in vacuo extracted with ethyl acetate (2×50 mL) The combined organic solution was dried over magnesium sulphate concentrated in vacuo The residue was purified by column chromatography on silica gel eluting with pentane:ethyl acetate 9:1 to 4:1