1-bromo-2-ethenylbenzene

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

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

Procedure: A 0.35M solution of 2-lithiostyrene was prepared dropwise addition of nBuLi to a -78° C. solution of 2-bromostyrene in 5:1 THF:diethyl ether.

Conditions: temp:-65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromostyrene (115 mmol) in dry tetrahydrofuran (200 ml) at -65° C. under nitrogen was added dropwise n-butyllithium (115 mmol) in hexane. The reaction mixture was stirred at -65° C. for an additional hour and a solution of N-formylpiperidine (125 mmol) in tetrahydrofuran (50 ml) was added dropwise. The reaction mixture was allowed to warm to ambient temperature overnight. The reaction mixture was cooled to 0° C. and then quenched with saturated ammonium chloride (50 ml). The reaction mixture was extracted with diethyl ether (2×50 ml) and the combined organic phases were washed with 3N hydrochloric acid (2×50 ml), saturated aqueous sodium bicarbonate (50 ml), and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to yield the Compound 2a which was directly used in the next reaction. to warm to ambient temperature overnight The reaction mixture was cooled to 0° C. quenched with saturated ammonium chloride (50 ml) The reaction mixture was extracted with diethyl ether (2×50 ml) the combined organic phases were washed with 3N hydrochloric acid (2×50 ml), saturated aqueous sodium bicarbonate (50 ml), and brine dried over anhydrous sodium sulfate filtered The filtrate was concentrated in vacuo

Conditions: temp:-65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromostyrene (115 mmol) in dry tetrahydrofuran (200 ml) at -65° C. under nitrogen was added dropwise n-butyllithium (115 mmol) in hexane. The reaction mixture was stirred at -65° C. for an additional hour and a solution of N-formylpiperidine (125 mmol) in tetrahydrofuran (50 ml) was added dropwise. The reaction mixture was allowed to warm to ambient temperature overnight. The reaction mixture was cooled to 0° C. and then quenched with saturated ammonium chloride (50 ml). The reaction mixture was extracted with diethyl ether (2×50 ml) and the combined organic phases were washed with 3N hydrochloric acid (2×50 ml), saturated aqueous sodium bicarbonate (50 ml), and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to yield the Compound 2a which was directly used in the next reaction. to warm to ambient temperature overnight The reaction mixture was cooled to 0° C. quenched with saturated ammonium chloride (50 ml) The reaction mixture was extracted with diethyl ether (2×50 ml) the combined organic phases were washed with 3N hydrochloric acid (2×50 ml), saturated aqueous sodium bicarbonate (50 ml), and brine dried over anhydrous sodium sulfate filtered The filtrate was concentrated in vacuo

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

Procedure: A 0.35M solution of 2-lithiostyrene was prepared dropwise addition of nBuLi to a -78° C. solution of 2-bromostyrene in 5:1 THF:diethyl ether.

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

Procedure: 1-Bromo-2-vinylbenzene (2.8146 g, 15.38 mmol) was azeotropped by dry benzene twice before taken up in THF (50 ml). The solution was cooled to −78° C. BuLi (6.77 ml, 16.91 mmol) was added to the reaction mixture at −78° C. and stirred for 20 min at this temperature. pent-4-enal (1.670 ml, 16.91 mmol) was added to the reaction mixture and stirred for 4 hours while the bath temperature gradually warmed up. Chlorotriisopropylsilane (3.58 ml, 16.91 mmol) was added to the reaction mixture and the reaction was stirred overnight while the reaction was warmed up to room temperature. The solvent was mostly removed via vacuum and the crude was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, dried (Na2SO4), filtered and concentrated. The product was obtained by flash column eluted with ether in hexane from 0 to 30% (3.9 g, 74% yield). MS (ESI)[M+H+]=346.46. stirred for 4 hours while the bath temperature gradually warmed up the reaction was stirred overnight while the reaction was warmed up to room temperature The solvent was mostly removed via vacuum the crude was partitioned between ethyl acetate and water The ethyl acetate layer was separated dried (Na2SO4) filtered concentrated The product was obtained by flash column eluted with ether in hexane from 0 to 30% (3.9 g, 74% yield)

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 20 ml solution of 50% sodium hydroxide was added dropwise to 2-bromostyrene (10.0 g, 54.9 mmol) in 100 ml of chloroform. The reaction mixture was warmed to 45° C. for 1 hour. After cooling the solution was separated and the organic layer was dried over magnesium sulfate and concentrated. The resulting liquid was flash chromatographed, affording 11.6 g of the desired compound. After cooling the solution was separated the organic layer was dried over magnesium sulfate concentrated chromatographed

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

Procedure: To a stirred solution of 1-bromo-2-vinylbenzene (4.14 g, 22.6 mmol) and 4-methylmorpholine N-oxide in acetonitrile (20 mL) and water (10 mL) was added a 2.5% solution of osmium tetroxide in 2-methyl-2-propanol (2 mL) at room temperature and the mixture was stirred for 24 h at the same temperature. The reaction mixture was quenched by the addition of sodium hydrosulfate, and diluted with water, then extracted with ethyl acetate. The organic layer washed with diluted hydrochloric acid aqueous solution and brine, dried over sodium sulfate, and evaporated to afford 5.01 g (quant.) of the title compound as a brown solid: The reaction mixture was quenched by the addition of sodium hydrosulfate diluted with water extracted with ethyl acetate The organic layer washed with diluted hydrochloric acid aqueous solution and brine dried over sodium sulfate evaporated

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 20 ml solution of 50% sodium hyroxide was added dropwise to 2-bromostyrene (10.0 g, 54.9 mmol) in 100 ml of chloroform. The reaction mixture was warmed to 45° C. for 1 hour. After cooling the solution was separated and the organic layer was dried over magnesium sulfate and concentrated. The resulting liquid was flash chromatographed, affording 11.6 g of the desired compound. After cooling the solution was separated the organic layer was dried over magnesium sulfate concentrated chromatographed

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 20 ml solution of 50% sodium hyroxide was added dropwise to 2-bromostyrene (10.0 g, 54.9 mmol) in 100 ml of chloroform. The reaction mixture was warmed to 45° C. for 1 hour. After cooling the solution was separated and the organic layer was dried over magnesium sulfate and concentrated. The resulting liquid was flash chromatographed, affording 11.6 g of the desired compound. After cooling the solution was separated the organic layer was dried over magnesium sulfate concentrated chromatographed

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

Procedure: A 0.35M solution of 2-lithiostyrene was prepared dropwise addition of nBuLi to a -78° C. solution of 2-bromostyrene in 5:1 THF:diethyl ether.

Conditions: temp:-65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromostyrene (115 mmol) in dry tetrahydrofuran (200 ml) at -65° C. under nitrogen was added dropwise n-butyllithium (115 mmol) in hexane. The reaction mixture was stirred at -65° C. for an additional hour and a solution of N-formylpiperidine (125 mmol) in tetrahydrofuran (50 ml) was added dropwise. The reaction mixture was allowed to warm to ambient temperature overnight. The reaction mixture was cooled to 0° C. and then quenched with saturated ammonium chloride (50 ml). The reaction mixture was extracted with diethyl ether (2×50 ml) and the combined organic phases were washed with 3N hydrochloric acid (2×50 ml), saturated aqueous sodium bicarbonate (50 ml), and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to yield the Compound 2a which was directly used in the next reaction. to warm to ambient temperature overnight The reaction mixture was cooled to 0° C. quenched with saturated ammonium chloride (50 ml) The reaction mixture was extracted with diethyl ether (2×50 ml) the combined organic phases were washed with 3N hydrochloric acid (2×50 ml), saturated aqueous sodium bicarbonate (50 ml), and brine dried over anhydrous sodium sulfate filtered The filtrate was concentrated in vacuo