1-but-3-enyl-3,5-difluorobenzene

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

Procedure: 0.41 mol 1,3 difluoro-5-(3-butenyl)-benzene was added to a dry round bottom flask with 300 ml anhydrous tetrahydrofuran. After cooling under a nitrogen atmosphere to −70° C. a solution of 0.46 mol of n-butyllithium in 280 ml hexane was added. After stirring at −70° C. for 30 minutes a mixture of 0.46 mol of Iodine in 200 ml tetrahydrofuran was added slowly over 2 hours. The reaction was left to warm to room temperature overnight. The reaction was quenched by pouring onto ice/hydrochloric acid mixture. The layers were separated and the aqueous layer extracted twice with diethyl ether (2×100 ml). The combined organic layers were washed with 50 g sodium thiosulphate in 200 ml water to remove excess iodine, then with water (2×50 ml) and dried over anhydrous sodium sulphate. Removal of the solvent yielded 126 g of the title compound as a beige solid. was added was added slowly over 2 hours The reaction was left to warm to room temperature overnight The reaction was quenched by pouring onto ice/hydrochloric acid mixture The layers were separated the aqueous layer extracted twice with diethyl ether (2×100 ml) The combined organic layers were washed with 50 g sodium thiosulphate in 200 ml water to remove excess iodine with water (2×50 ml) and dried over anhydrous sodium sulphate Removal of the solvent

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

Procedure: 0.41 mol 1,3 difluoro-5-(3-butenyl)-benzene was added to a dry round bottom flask with 300 ml anhydrous tetrahydrofuran. After cooling under a nitrogen atmosphere to −70° C. a solution of 0.46 mol of n-butyllithium in 280 ml hexane was added. After stirring at −70° C. for 30 minutes a mixture of 0.46 mol of Iodine in 200 ml tetrahydrofuran was added slowly over 2 hours. The reaction was left to warm to room temperature overnight. The reaction was quenched by pouring onto ice/hydrochloric acid mixture. The layers were separated and the aqueous layer extracted twice with diethyl ether (2×100 ml). The combined organic layers were washed with 50 g sodium thiosulphate in 200 ml water to remove excess iodine, then with water (2×50 ml) and dried over anhydrous sodium sulphate. Removal of the solvent yielded 126 g of the title compound as a beige solid. was added was added slowly over 2 hours The reaction was left to warm to room temperature overnight The reaction was quenched by pouring onto ice/hydrochloric acid mixture The layers were separated the aqueous layer extracted twice with diethyl ether (2×100 ml) The combined organic layers were washed with 50 g sodium thiosulphate in 200 ml water to remove excess iodine with water (2×50 ml) and dried over anhydrous sodium sulphate Removal of the solvent

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

Procedure: A 176 g portion of 3,5-difluorobenzyl bromide was dissolved in 300 ml of THF to which was subsequently added dropwise 450 ml of allyl magnesium chloride THF solution (2 mol/l) at room temperature. This was stirred for 1 hour and then mixed with 300 ml of water. This was extracted with 800 ml of hexane, washed twice with saturated brine and then dried with anhydrous sodium sulfate. After evaporation of the solvent, the resulting residue was distilled (79-82° C./20 mmHg) to obtain 104 g of 3,5-difluoro-1-(3-butenyl)benzene. This was extracted with 800 ml of hexane washed twice with saturated brine dried with anhydrous sodium sulfate After evaporation of the solvent the resulting residue was distilled (79-82° C./20 mmHg)

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

Procedure: A 176 g portion of 3,5-difluorobenzyl bromide was dissolved in 300 ml of THF to which was subsequently added dropwise 450 ml of allyl magnesium chloride THF solution (2 mol/l) at room temperature. This was stirred for 1 hour and then mixed with 300 ml of water. This was extracted with 800 ml of hexane, washed twice with saturated brine and then dried with anhydrous sodium sulfate. After evaporation of the solvent, the resulting residue was distilled (79-82° C./20 mmHg) to obtain 104 g of 3,5-difluoro-1-(3-butenyl)benzene. This was extracted with 800 ml of hexane washed twice with saturated brine dried with anhydrous sodium sulfate After evaporation of the solvent the resulting residue was distilled (79-82° C./20 mmHg)

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

Procedure: 0.41 mol 1,3 difluoro-5-(3-butenyl)-benzene was added to a dry round bottom flask with 300 ml anhydrous tetrahydrofuran. After cooling under a nitrogen atmosphere to −70° C. a solution of 0.46 mol of n-butyllithium in 280 ml hexane was added. After stirring at −70° C. for 30 minutes a mixture of 0.46 mol of Iodine in 200 ml tetrahydrofuran was added slowly over 2 hours. The reaction was left to warm to room temperature overnight. The reaction was quenched by pouring onto ice/hydrochloric acid mixture. The layers were separated and the aqueous layer extracted twice with diethyl ether (2×100 ml). The combined organic layers were washed with 50 g sodium thiosulphate in 200 ml water to remove excess iodine, then with water (2×50 ml) and dried over anhydrous sodium sulphate. Removal of the solvent yielded 126 g of the title compound as a beige solid. was added was added slowly over 2 hours The reaction was left to warm to room temperature overnight The reaction was quenched by pouring onto ice/hydrochloric acid mixture The layers were separated the aqueous layer extracted twice with diethyl ether (2×100 ml) The combined organic layers were washed with 50 g sodium thiosulphate in 200 ml water to remove excess iodine with water (2×50 ml) and dried over anhydrous sodium sulphate Removal of the solvent