| 82% |
With cesium fluoride; In dimethyl sulfoxide; at 140℃; for 10h; |
Compound 2a-1: 2-Fluoro-1-methyl-3-nitrobenzene; [Show Image] Cesium fluoride (97.5 g, 642 mmol) was added under nitrogen atmosphere to a solution of 2-chloro-1-methyl-3-nitrobenzene (73.4 g, 428 mmol) in DMSO (185 mL), and the mixture was stirred at 140°C for 10 hours. The reaction mixture was then poured into 0.5N hydrochloric acid and extracted twice with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate. A crude product was obtained by vacuum concentration, and then purified by reduced-pressure distillation (boiling point: 118 °C to 122°C/ 15 mm Hg) to yield the title compound (54.4 g, 82percent) as a yellow oil. 1H NMR (DMSO-d6, 270 MHz) delta (ppm): 7.96 (m, 1H), 7.73 (m, 1H), 7.34 (t, J = 8.2 Hz, 1H), 2.35 (d, J = 2.4 Hz, 3H). HPLC Rt = 2.03 min.HPLC conditions: Column: Combi ODS (ODS, 5 mum, 4.6 mm I.D. .x. 50 mm, Wako Pure Chemical Industries), COSMOSIL (ODS, 5 mum, 4.6 mm I.D. .x. 50 mm, Nacalai Tesque), Intersil C18 (ODS, 5 mum, 4.6 mm I.D. .x. 50 mm, GL Sciences), or SunFire C18 (ODS, 5 mum, 4.6 mm I.D. .x. 50 mm, Waters);Mobile phase: Water (A) containing 0.05percent trifluoroacetic acid, and acetonitrile (B) containing 0.05percent trifluoroacetic acid;Elution method: Stepwise solvent gradient elution (Solvent composition was changed from 10percent B to 95percent B in 3.5 minutes, then changed to 10percent B in 1 minute, and kept at 10percent B for 0.5 minute);Flow rate: 4.0 mL/min. |
| 82% |
With cesium fluoride; In dimethyl sulfoxide; |
2-Fluoro-1-methyl-3-nitrobenzene Cesium fluoride (97.5 g, 642 mmol) was added under nitrogen atmosphere to a solution of 2-chloro-1-methyl-3-nitrobenzene (73.4 g, 428 mmol) in DMSO (185 mL), and the mixture was stirred at 140°C for 10 hours. The reaction mixture was then poured into 0.5N hydrochloric acid and extracted twice with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate. A crude product was obtained by vacuum concentration, and then purified by reduced-pressure distillation (boiling point: 118 °C to 122°C/ 15 mm Hg) to yield the title compound (54.4 g, 82percent) as a yellow oil. 1H NMR (DMSO-d6, 270 MHz) delta (ppm): 7.96 (m, 1H), 7.73 (m, 1H), 7.34 (t, J = 8.2 Hz, 1H), 2.35 (d, J = 2.4 Hz, 3H). HPLC Rt = 2.03 min. HPLC conditions: Column: Combi ODS (ODS, 5 mum, 4.6 mm I.D. * 50 mm, Wako Pure Chemical Industries), COSMOSIL (ODS, 5 mum, 4.6 mm I.D. * 50 mm, Nacalai Tesque), Intersil C18 (ODS, 5 mum, 4.6 mm I.D. * 50 mm, GL Sciences), or SunFire C18 (ODS, 5 mum, 4.6 mm I.D. * 50 mm, Waters); Mobile phase: Water (A) containing 0.05percent trifluoroacetic acid, and acetonitrile (B) containing 0.05percent trifluoroacetic acid; |
| 82% |
With cesium fluoride; In dimethyl sulfoxide; at 140℃; for 10h;Inert atmosphere; |
Cesium fluoride (97.5 g, 642 mmol) was added under nitrogen atmosphere to a solution of 2-chloro-1-methyl-3-nitrobenzene(73.4 g, 428 mmol) in DMSO (185 mL), and the mixture was stirred at 140° C. for 10 hours. The reaction mixture was then poured into 0.5N hydrochloric acid and extracted twice with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate. A crude product was obtained by vacuum concentration, and then purified by reduced-pressure distillation (boilingpoint: 118° C. to 122° C./15 mm Hg) to yield the title compound (54.4 g, 82percent)as a yellow oil. |
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