4-bromo-2-chloro-1-ethenylbenzene

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

Procedure: Using a procedure analogous to that used to prepare 30B, 61A (5 g, 23 mmol) was heated in a pressure vessel with 9-BBN at 100° C. for 10 h and worked up as in 30B to yield 61B (2.9 g, 54%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.95 (t, J=6.59 Hz, 2 H) 3.85 (t, J=6.59 Hz, 2 H) 7.14 (d, J=7.91 Hz, 1 H) 7.33 (dd, J=8.13, 1.98 Hz, 1 H) 7.52 (d, J=2.20 Hz, 1 H).

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

Procedure: Using a procedure analogous to that used to prepare 30B, 61A (5 g, 23 mmol) was heated in a pressure vessel with 9-BBN at 100° C. for 10 h and worked up as in 30B to yield 61B (2.9 g, 54%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.95 (t, J=6.59 Hz, 2 H) 3.85 (t, J=6.59 Hz, 2 H) 7.14 (d, J=7.91 Hz, 1 H) 7.33 (dd, J=8.13, 1.98 Hz, 1 H) 7.52 (d, J=2.20 Hz, 1 H).

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

Procedure: Using a procedure analogous to that used to prepare 30A, 4-bromo-2-chloro-1-iodobenzene (8 g, 25 mmol) was reacted with trimethyl(vinyl)silane in a pressure vessel at 160° C. for 1 h and worked up in a manner similar as in 30A to yield 61A (5.2 g, 96%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 5.41 (d, J=11.86 Hz, 1 H) 7.02 (dd, J=17.36, 11.21 Hz, 1 H) 7.35 (dd, 1 H) 7.41 (d, 1 H) 7.52 (d, J=1.76 Hz, 1 H).

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

Procedure: A solution of 4-bromo-2-chloro-1-ethenylbenzene (883 mg), iron(II) acetate (7 mg) and 5% rhodium-activated carbon (167 mg) in tetrahydrofuran (17 mL) was stirred at room temperature for three hours in a hydrogen atmosphere. The reaction solution was filtered through celite and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane only) to give the title compound as a colorless oil (414 mg, 46%). The reaction solution was filtered through celite the filtrate was evaporated under reduced pressure The residue was purified by silica gel column chromatography (hexane only)

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

Procedure: Using a procedure analogous to that used to prepare 30B, 61A (5 g, 23 mmol) was heated in a pressure vessel with 9-BBN at 100° C. for 10 h and worked up as in 30B to yield 61B (2.9 g, 54%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.95 (t, J=6.59 Hz, 2 H) 3.85 (t, J=6.59 Hz, 2 H) 7.14 (d, J=7.91 Hz, 1 H) 7.33 (dd, J=8.13, 1.98 Hz, 1 H) 7.52 (d, J=2.20 Hz, 1 H).

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

Procedure: Using a procedure analogous to that used to prepare 30A, 4-bromo-2-chloro-1-iodobenzene (8 g, 25 mmol) was reacted with trimethyl(vinyl)silane in a pressure vessel at 160° C. for 1 h and worked up in a manner similar as in 30A to yield 61A (5.2 g, 96%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 5.41 (d, J=11.86 Hz, 1 H) 7.02 (dd, J=17.36, 11.21 Hz, 1 H) 7.35 (dd, 1 H) 7.41 (d, 1 H) 7.52 (d, J=1.76 Hz, 1 H).