(Z)-1-bromopent-2-ene

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

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

Procedure: The title compound (trans) was prepared as a yellow-orange oil in 85.1% yeild in a similar procedure to that described in Referential Example 9 by using methyl 3-formyl-4,5-dimethylpyrrole-2-carboxylate and 1-bromo-2-pentene (trans).

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

Procedure: Pent-2-enyl bromide (18.5 g) was added dropwise to a stirred refluxing mixture of imidazole (10 g) and sodium bicarbonate (12.4 g) in methanol (50 ml). After addition was complete, the mixture was stirred under reflux for a further 24 hours. The mixture was filtered to remove unsoluble material and the filtrate evaporated to remove solvent. Residue taken in 2N-HCl (150 ml) and washed with ether (50 ml). The aqueous layer was basified with 10N NaOH and extracted with chloroform (3×50 ml). Combined extracts dried over anhydrous MgSO4 and chloroform removed under vacuum to leave crude product which was purified on silica gel column (EtOAc/MeOH 9:1 was used as eluent). Product fractions were collected; total weight 4.9 g. 1.0 g was distilled under vacuum; yield 1.08 g. B.p. 134° C./15 mmHg. Micro analysis: C8H12N2 requires C,70.59; H,8.82; N,20.59. Found: C,69.72, H,8.88; N,20.43. refluxing After addition under reflux for a further 24 hours The mixture was filtered to remove unsoluble material the filtrate evaporated to remove solvent washed with ether (50 ml) extracted with chloroform (3×50 ml) Combined extracts dried over anhydrous MgSO4 and chloroform removed under vacuum to leave crude product which was purified on silica gel column (EtOAc/MeOH 9:1 was used as eluent) Product fractions were collected 1.0 g was distilled under vacuum

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

Procedure: A solution of 1.00 g (0.00287 mol) of 1,1,2-tribromo-2-pentyl-cyclopropane in 4 ml of tetrahydrofuran was placed under an inert atmosphere of nitrogen via a Firestone valve. To this mixture, cooling in an ice water bath, was added via syringe 3.58 ml (0.00861 mol) of 1.6M n-butyllithium in hexanes. After 30 minutes, 0.432 ml (0.00287 mol) of tetramethylethylene diamine and 0.339 ml (0.00287 mol) of 1-bromo-2-pentene were added by syringe. The reaction stirred for one hour while warming to room temperature, then for three hours at room temperature. To the resulting mixture was added 2 ml of water. This residue was extracted with diethyl ether. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo to yield 0.200 g (39.1% of theory) of 1-pent-2-enyl-2-pentyl-cyclopropene as an oil. To this mixture, cooling in an ice water bath for three hours at room temperature This residue was extracted with diethyl ether The resulting mixture was transferred to a separatory funnel the phases were separated The organic layer was dried over MgSO4 filtered The solvent was removed from the filtrate in vacuo

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

Procedure: The captioned compound was synthesized from 3-N-(4-chlorophenyl)-4-methoxyisophthalamide and 1-bromo-2-pentene by the same procedure as in the manufacturing method described in Example 1-1-2.

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

Procedure: The captioned compound was synthesized from 3-N-(4-chlorophenyl)-4-methoxyisophthalamide and 1-bromo-2-pentene by the same procedure as in the manufacturing method described in Example 1-1-2.

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

Procedure: The captioned compound was synthesized from 3-N-(4-chlorophenyl)-4-methoxyisophthalamide and 1-bromo-2-pentene by the same procedure as in the manufacturing method described in Example 1-1-2.

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

Procedure: The captioned compound was synthesized from 3-N-(4-chlorophenyl)-4-methoxyisophthalamide and 1-bromo-2-pentene by the same procedure as in the manufacturing method described in Example 1-1-2.

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

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

Procedure: An ice-cold solution of 2-iodophenol (6.00 g, 272 mmol) in DMF (100 mL) was added dropwise to a solution of NaH (1.30 g, 54.4 mmol) in DMF. 1-Bromo-pent-2-ene (4.87 g, 327 mmol) was then added. The mixture slowly warmed to room temperature overnight. The reaction was quenched with water (50 mL) and the mixture was extracted with CH2Cl2 (3×). The combined organics were washed with brine and dried over Na2SO4 to give the title compound (8.50 g, 99%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.75 (dd, J=7.5, 1.2, Hz, 1H), 7.36-7.30 (m, 1H), 6.98 (d, J=8.1 Hz, 1H), 6.76-6.71 (m, 1H), 6.01-5.89 (m, 1H), 5.67 (t, J=5.7 Hz, 1H), 4.54 (d, J=5.7 Hz, 2H), 2.08 (t, J=7.5 Hz, 2H), The reaction was quenched with water (50 mL) the mixture was extracted with CH2Cl2 (3×) The combined organics were washed with brine dried over Na2SO4

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

Procedure: An ice-cold solution of 2-iodophenol (6.00 g, 272 mmol) in DMF (100 mL) was added dropwise to a solution of NaH (1.30 g, 54.4 mmol) in DMF. 1-Bromo-pent-2-ene (4.87 g, 327 mmol) was then added. The mixture slowly warmed to room temperature overnight. The reaction was quenched with water (50 mL) and the mixture was extracted with CH2Cl2 (3×). The combined organics were washed with brine and dried over Na2SO4 to give the title compound (8.50 g, 99%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.75 (dd, J=7.5, 1.2, Hz, 1H), 7.36-7.30 (m, 1H), 6.98 (d, J=8.1 Hz, 1H), 6.76-6.71 (m, 1H), 6.01-5.89 (m, 1H), 5.67 (t, J=5.7 Hz, 1H), 4.54 (d, J=5.7 Hz, 2H), 2.08 (t, J=7.5 Hz, 2H), 0.98 (t, J=7.5 Hz, 3H). The reaction was quenched with water (50 mL) the mixture was extracted with CH2Cl2 (3×) The combined organics were washed with brine dried over Na2SO4

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

Procedure: The title compound (trans) was prepared as a yellow-orange oil in 85.1% yeild in a similar procedure to that described in Referential Example 9 by using methyl 3-formyl-4,5-dimethylpyrrole-2-carboxylate and 1-bromo-2-pentene (trans).