2,3,5,6-TETRABROMO-P-XYLENE

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To tetrabromo para-xylene (2.1 g, 5.0 mmol) and furan (4 g, 58.8 mmol) in PhMe (55 mL) at −78° C. was added BuLi (2.2 mL, 2.5M in hexanes, 5.5 mmol) dropwise. The reaction was stirred for two hours at −78° C. and the allowed to warm to rt. After 3 hours, MeOH (2 mL) was added and the reaction mixture was poured into water. The organic layer was separated and the aqueous layer was extracted three times with Et2O. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silca gel gave 26 (185 mg, 50%) as a white solid. The spectral data correlates well with the literature values. 22 to warm to rt After 3 hours The organic layer was separated the aqueous layer was extracted three times with Et2O The combined organic layers were washed with brine dried over MgSO4 concentrated

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To tetrabromo para-xylene (2.1 g, 5.0 mmol) and furan (4 g, 58.8 mmol) in PhMe (55 mL) at −78° C. was added BuLi (2.2 mL, 2.5M in hexanes, 5.5 mmol) dropwise. The reaction was stirred for two hours at −78° C. and the allowed to warm to rt. After 3 hours, MeOH (2 mL) was added and the reaction mixture was poured into water. The organic layer was separated and the aqueous layer was extracted three times with Et2O. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silica gel gave 26 (185 mg, 50%) as a white solid. The spectral data correlates well with the literature values.22 to warm to rt After 3 hours The organic layer was separated the aqueous layer was extracted three times with Et2O The combined organic layers were washed with brine dried over MgSO4 concentrated

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To tetrabromo para-xylene (2.1 g, 5.0 mmol) and furan (4 g, 58.8 mmol) in PhMe (55 mL) at −78° C. was added BuLi (2.2 mL, 2.5M in hexanes, 5.5 mmol) dropwise. The reaction was stirred for two hours at −78° C. and the allowed to warm to rt. After 3 hours, MeOH (2 mL) was added and the reaction mixture was poured into water. The organic layer was separated and the aqueous layer was extracted three times with Et2O. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silca gel gave 26 (185 mg, 50%) as a white solid. The spectral data correlates well with the literature values. 22 to warm to rt After 3 hours The organic layer was separated the aqueous layer was extracted three times with Et2O The combined organic layers were washed with brine dried over MgSO4 concentrated

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To tetrabromo para-xylene (2.1 g, 5.0 mmol) and furan (4 g, 58.8 mmol) in PhMe (55 mL) at −78° C. was added BuLi (2.2 mL, 2.5M in hexanes, 5.5 mmol) dropwise. The reaction was stirred for two hours at −78° C. and the allowed to warm to rt. After 3 hours, MeOH (2 mL) was added and the reaction mixture was poured into water. The organic layer was separated and the aqueous layer was extracted three times with Et2O. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silca gel gave 26 (185 mg, 50%) as a white solid. The spectral data correlates well with the literature values. 22 to warm to rt After 3 hours The organic layer was separated the aqueous layer was extracted three times with Et2O The combined organic layers were washed with brine dried over MgSO4 concentrated

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a glass resin flask, a mixture of 1000 parts bromine and 3 parts of aluminum tribromide was cooled at 5° C and 83 parts of p-xylene were added dropwise with rapid stirring and continued cooling. After adding about 3/4 of the xylene, the reaction mixture became viscous forming large chunks of product. The mixture was diluted with 454 parts of bromine and the temperature was brought to 30° C. The heating and stirring gradually broke down the chunks of product to a fine powder. The mixture was then cooled to 15° C and the remaining xylene was added. Most of the excess bromine was removed by distillation. The solid was removed from the reaction flask and leached with cold methanol to remove excess bromine. The product was then dissolved in hot benzene and filtered. The solvent was then driven off and 323 parts (98.3% yield) of tetrabromo-p-xylene was obtained as crystals having the melting point of 253°-254° C. continued cooling was brought to 30° C The heating and stirring gradually The mixture was then cooled to 15° C Most of the excess bromine was removed by distillation The solid was removed from the reaction flask to remove excess bromine The product was then dissolved in hot benzene filtered

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a glass resin flask, a mixture of 1000 parts bromine and 3 parts of aluminum tribromide was cooled at 5° C and 83 parts of p-xylene were added dropwise with rapid stirring and continued cooling. After adding about 3/4 of the xylene, the reaction mixture became viscous forming large chunks of product. The mixture was diluted with 454 parts of bromine and the temperature was brought to 30° C. The heating and stirring gradually broke down the chunks of product to a fine powder. The mixture was then cooled to 15° C and the remaining xylene was added. Most of the excess bromine was removed by distillation. The solid was removed from the reaction flask and leached with cold methanol to remove excess bromine. The product was then dissolved in hot benzene and filtered. The solvent was then driven off and 323 parts (98.3% yield) of tetrabromo-p-xylene was obtained as crystals having the melting point of 253°-254° C. continued cooling was brought to 30° C The heating and stirring gradually The mixture was then cooled to 15° C Most of the excess bromine was removed by distillation The solid was removed from the reaction flask to remove excess bromine The product was then dissolved in hot benzene filtered

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To tetrabromo para-xylene (2.1 g, 5.0 mmol) and furan (4 g, 58.8 mmol) in PhMe (55 mL) at −78° C. was added BuLi (2.2 mL, 2.5M in hexanes, 5.5 mmol) dropwise. The reaction was stirred for two hours at −78° C. and the allowed to warm to rt. After 3 hours, MeOH (2 mL) was added and the reaction mixture was poured into water. The organic layer was separated and the aqueous layer was extracted three times with Et2O. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silca gel gave 26 (185 mg, 50%) as a white solid. The spectral data correlates well with the literature values.22 to warm to rt After 3 hours The organic layer was separated the aqueous layer was extracted three times with Et2O The combined organic layers were washed with brine dried over MgSO4 concentrated

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To tetrabromo para-xylene (2.1 g, 5.0 mmol) and furan (4 g, 58.8 mmol) in PhMe (55 mL) at −78° C. was added BuLi (2.2 mL, 2.5M in hexanes, 5.5 mmol) dropwise. The reaction was stirred for two hours at −78° C. and the allowed to warm to rt. After 3 hours, MeOH (2 mL) was added and the reaction mixture was poured into water. The organic layer was separated and the aqueous layer was extracted three times with Et2O. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silica gel gave 26 (185 mg, 50%) as a white solid. The spectral data correlates well with the literature values.22 to warm to rt After 3 hours The organic layer was separated the aqueous layer was extracted three times with Et2O The combined organic layers were washed with brine dried over MgSO4 concentrated