2-(4-iodophenyl)acetyl chloride

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under an argon atmosphere, 4-iodophenylacetyl chloride (12) obtained above was dissolved in THF (2 mL) and acetonitrile (2 mL) and cooled to 0° C. To this was slowly added a solution of trimethylsilyldiazomethane in diethyl ether (2.0 M, 4.00 mL, 8.00 mmol), which was stirred overnight (14 h) after warming up to room temperature. After concentrating under reduced pressure, the residue was purified by silica gel flash column chromatography (n-hexane/diethyl ether=1/1) to give 1-diazo-3-(4-iodophenyl)propan-2-one (13) as a pale yellow solid (635 mg, 4.44 mmol, 55.5%, 2 steps). After concentrating under reduced pressure the residue was purified by silica gel flash column chromatography (n-hexane/diethyl ether=1/1)

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under an argon atmosphere, to 4-iodophenylacetic acid (11) (prepared by the process described in Chen, Q.-H. et al., Bioorg. Med. Chem., 14, 7898-7909 (2006)) (1.06 g, 4.05 mmol) was added thionyl chloride (5.00 mL, 68.6 mmol) and heated to reflux (100° C.) for 1.5 h. After cooling to room temperature, the mixture was concentrated under reduced pressure to give 4-iodophenylacetyl chloride (12) as a brown oily crude product. heated After cooling to room temperature the mixture was concentrated under reduced pressure

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under an argon atmosphere, to 4-iodophenylacetic acid (11) (prepared by the process described in Chen, Q.-H. et al., Bioorg. Med. Chem., 14, 7898-7909 (2006)) (1.06 g, 4.05 mmol) was added thionyl chloride (5.00 mL, 68.6 mmol) and heated to reflux (100° C.) for 1.5 h. After cooling to room temperature, the mixture was concentrated under reduced pressure to give 4-iodophenylacetyl chloride (12) as a brown oily crude product. heated After cooling to room temperature the mixture was concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under an argon atmosphere, 4-iodophenylacetyl chloride (12) prepared above was dissolved in tetrahydrofuran (THF) (2 mL) and acetonitrile (2 mL) and cooled to 0° C. To this was slowly added a solution of trimethylsilyldiazomethane in diethyl ether (2.0 M, 4.00 mL, 8.00 mmol), which was stirred overnight (14 h) after warming up to room temperature. After concentrating under reduced pressure, the residue was purified by silica gel flash column chromatography (n-hexane/diethyl ether=1/1) to give 1-diazo-3-(4-iodophenyl)propan-2-one (13) as a pale yellow solid (635 mg, 2.22 mmol, 54.9%, 2 steps). After concentrating under reduced pressure the residue was purified by silica gel flash column chromatography (n-hexane/diethyl ether=1/1)

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under an argon atmosphere, to 4-iodophenylacetic acid (11) (prepared by the process described in Chen, Q.-H. et al., Bioorg. Med. Chem. 14, 7898-7909 (2006)) (1.06 g, 4.05 mmol) was added thionyl chloride (5.00 mL, 68.6 mmol) and heated to reflux (100° C.) for 1.5 h. After cooling to room temperature, the mixture was concentrated under reduced pressure to give 4-iodophenylacetyl chloride (12) as a brown oily crude product, which was used in the next reaction without further purification. heated After cooling to room temperature the mixture was concentrated under reduced pressure

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under an argon atmosphere, to 4-iodophenylacetic acid (11) (prepared by the process described in Chen, Q.-H. et al., Bioorg. Med. Chem. 14, 7898-7909 (2006)) (1.06 g, 4.05 mmol) was added thionyl chloride (5.00 mL, 68.6 mmol) and heated to reflux (100° C.) for 1.5 h. After cooling to room temperature, the mixture was concentrated under reduced pressure to give 4-iodophenylacetyl chloride (12) as a brown oily crude product, which was used in the next reaction without further purification. heated After cooling to room temperature the mixture was concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Concentrated aqueous ammonia (density, 0.88 g/cm3) was added to a solution of 4-iodophenylacetyl chloride (2.80 g) in ether (30 ml) and the mixture was stirred at ambient temperature for 15 minutes. The product, 4-iodophenylacetamide, was obtained as a colourless crystalline solid (2.36 g), m.p: 200-204° C.; NMR: 3.34(2H,s), 6.87(H,bs), 7.44(2H,bs), 7.04-7.68(4H,AB); m/z 262(M+H).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Thionyl chloride (39.53) and DMF (2 drops) were added to a solution of 4-iodophenylacetic acid (26.2 g), in dichloromethane (150 ml). The reaction mixture was stirred at ambient temperature for 18 hours and the solvent removed by evaporation to give 4-iodophenylacetyl chloride as an oil (23 g) which was purified by vacuum distillation; b.p. 118-119° C. (0.35 mmMg) the solvent removed by evaporation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-Butylamine (1.83 g) was added to a solution of 4-iodophenylacetyl chloride (2.80 g) in ether (25 ml), and the reaction mixture was stirred at ambient temperature for 5 minutes. The reaction mixture was then partitioned between water (30 ml) and ethyl acetate (50 ml). The organic layer was washed with 2M aqueous hydrochloric acid (25 ml), water (30 ml), brine (25 ml), dried (MgSO4), and evaporated to give N-1-butyl, (4-iodophenyl)acetamide, as a colourless crystalline solid, (2.9 g), mp.: 100-102° C., NMR: 0.82-0.88(3H,t), 1.18-1.43(4H,m), 3.00-3.06(2H,q), 3.35(2H,s), 7.03-7.67(4H,AB), 7.97(H,bt); m/z 318 (M+H). The reaction mixture was then partitioned between water (30 ml) and ethyl acetate (50 ml) The organic layer was washed with 2M aqueous hydrochloric acid (25 ml), water (30 ml), brine (25 ml) dried (MgSO4) evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-Butylamine (1.83 g) was added to a solution of 4-iodophenylacetyl chloride (2.80 g) in ether (25 ml), and the reaction mixture was stirred at ambient temperature for 5 minutes. The reaction mixture was then partitioned between water (30 ml) and ethyl acetate (50 ml). The organic layer was washed with 2M aqueous hydrochloric acid (25 ml), water (30 ml), brine (25 ml), dried (MgSO4), and evaporated to give N-1-butyl, (4-iodophenyl)acetamide, as a colourless crystalline solid, (2.9 g), mp.: 100-102° C., NMR: 0.82-0.88(3H,t), 1.18-1.43(4H,m), 3.00-3.06(2H,q), 3.35(2H,s), 7.03-7.67(4H,AB), 7.97(H,bt); m/z 318 (M+H). The reaction mixture was then partitioned between water (30 ml) and ethyl acetate (50 ml) The organic layer was washed with 2M aqueous hydrochloric acid (25 ml), water (30 ml), brine (25 ml) dried (MgSO4) evaporated