2-(2-iodophenyl)acetonitrile

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

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

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

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

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

Procedure: A solution of 2-(2-iodophenyl)acetonitrile (2.82 g) in a mixture of 1:1 (v/v) ethanol/water (70 ml) was treated with sodium hydroxide (2.4 g) and stirred at reflux for 4 hours. The resultant solution was cooled to ambient temperature, concentrated to 30 ml, diluted with water (100 ml) and washed with ethyl acetate (2×100 ml). The organic layers were combined and extracted with 2M aqueous sodium hydroxide solution (100 ml). The aqueous layer was acidified to pH 1 with concentrated hydrochloric acid and filtered. The solid collected was washed with water and vacuum dried to give 2-(2-iodophenyl)acetic acid (1.45 g) as a solid, m.p. 110-113° C.; microanalysis; found: C, 36.9; H; 2.7%; C8H7IO2 requires: C, 36.7; H, 2.7%; NMR: 3.7(2H, s), 7.0(1H, m), 7.4(2H, m), 7.8(2H, d); 12.5(1H, br s). at reflux for 4 hours concentrated to 30 ml diluted with water (100 ml) washed with ethyl acetate (2×100 ml) extracted with 2M aqueous sodium hydroxide solution (100 ml) filtered The solid collected was washed with water and vacuum dried

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

Procedure: A solution of 2-(2-iodophenyl)acetonitrile (2.82 g) in a mixture of 1:1 (v/v) ethanol/water (70 ml) was treated with sodium hydroxide (2.4 g) and stirred at reflux for 4 hours. The resultant solution was cooled to ambient temperature, concentrated to 30 ml, diluted with water (100 ml) and washed with ethyl acetate (2×100 ml). The organic layers were combined and extracted with 2M aqueous sodium hydroxide solution (100 ml). The aqueous layer was acidified to pH 1 with concentrated hydrochloric acid and filtered. The solid collected was washed with water and vacuum dried to give 2-(2-iodophenyl)acetic acid (1.45 g) as a solid, m.p. 110-113° C.; microanalysis; found: C, 36.9; H; 2.7%; C8H7IO2 requires: C, 36.7; H, 2.7%; NMR: 3.7(2H, s), 7.0(1H, m), 7.4(2H, m), 7.8(2H, d); 12.5(1H, br s). at reflux for 4 hours concentrated to 30 ml diluted with water (100 ml) washed with ethyl acetate (2×100 ml) extracted with 2M aqueous sodium hydroxide solution (100 ml) filtered The solid collected was washed with water and vacuum dried

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

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

Procedure: To a suspension of (2-iodo-phenyl)-acetonitrile (Aldrich, 2.4 g, 10 mmol) and 2,3-difluorophenylboronic acid (Aldrich, 2.4 g, 15 mmol) in anhydrous methanol (10 mL) and toluene (20 mL) was added Cs2CO3 (9.8 g, 30 mmol). The mixture was degassed with nitrogen, followed by the addition of tetrakis(triphenylphosphine)palladium (1.2 g, 1 mmol). The mixture was degassed with nitrogen

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

Procedure: 2-(2-Iodophenyl)acetonitrile (3.0 g, 12 mmol) and sodium tert-butoxide (3.6 g, 37 mmol) were stirred in 20 mL of DMF, and MeI (0.77 mL, 12 mmol) was added dropwise. The reaction was then stirred for 3 hours. The solvent was removed under vacuum. The crude residue was purified by silica flash chromatography 0-15% EtOAc/hexanes. The solvent was removed under vacuum The crude residue was purified by silica flash chromatography 0-15% EtOAc/hexanes

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

Procedure: The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (74 mg, 0.39 mmol) and 2-(2-iodophenyl)acetonitrile (60 μL, 0.43 mmol) according to the general procedure IC to give 74 mg (62%) of an orange solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:4). Rf=0.08 (EtOAc:PE, 1:4); 1H NMR (CDCl3) δ 7.55-7.46 (m, 4H), 7.37-7.34 (m, 2H), 7.21 (d, J=8.4 Hz, 2H), 3.96 (s, 2H), 3.67 (s, 3H), 2.97 (t, J=7.7 Hz, 2H), 2.64 (t, J=7.5 Hz, 2H); 13C NMR (CDCl3) δ 173.0, 141.6, 132.3, 131.7, 131.6, 128.9, 128.5, 128.1, 122.9, 120.4, 117.4, 95.6, 85.7, 51.7, 35.3, 30.8, 22.7; ESI-MS m/z 326.1 (M+Na+).

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

Procedure: As described for example 11c, 4-ethynyl-5-methyl-3-phenyl-isoxazole (110 mg, 0.60 mmol) was converted (using 2-iodo-phenylacetonitrile instead of 2-chloro-4-iodopyridine) to the title compound (SiO2, heptane:ethyl acetate=100:0 to 80:20, 156 mg, 87%) which was obtained as a light brown oil. MS: m/e=375.1 [M+H]+.

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

Procedure: 2-(2-Iodophenyl)acetonitrile (3.0 g, 12 mmol) and sodium tert-butoxide (3.6 g, 37 mmol) were stirred in 20 mL of DMF, and MeI (0.77 mL, 12 mmol) was added dropwise. The reaction was then stirred for 3 hours. The solvent was removed under vacuum. The crude residue was purified by silica flash chromatography 0-15% EtOAc/hexanes. The solvent was removed under vacuum The crude residue was purified by silica flash chromatography 0-15% EtOAc/hexanes