1-(bromomethyl)-3-chloro-2-methoxybenzene

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: A solution of 1-chloro-2-methoxy-3-methyl-benzene (13.40 g, 85.60 mmol), NBS (15.30 g, 86.00 mmol) and a catalytic amount of benzoyl peroxide (150 mg) in CCl4 was refluxed for 30 minutes. The reaction mixture was cooled to room temperature and filtered. The precipitate was washed with pentane. The solvent was distilled off and the residue was purified by column chromatography using pentane as the eluant to afford the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 4.00 (s, 3H), 4.56 (s, 2H), 7.04 (t, J=7.62 Hz, 1H), 7.29 (dd, J=7.62 Hz, 1H), 7.34 (dd, J=7.92 Hz, 1H). filtered The precipitate was washed with pentane The solvent was distilled off the residue was purified by column chromatography

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

実験手順: 2-(3-chloro-2-methoxyphenyl)acetonitrile. A solution of 1-(bromomethyl)-3-chloro-2-methoxybenzene (30.8 g, 131 mmol) in EtOH (150 mL) at RT and under N2 was treated with an aq. solution of NaCN (12.8 g, 262 mmol in 50 mL H2O) and the mixture was heated to 100° C. for 3 h. The reaction was then cooled to RT and taken up in Et2O. The mixture was washed with H2O and brine, and the aq. phase was extracted again with Et2O. The combined org. layers dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, Hexane to Hexane/AcOEt 4:1) to afford the title compound (15.8 g) as brown oil. UPLC (2 min) rt 1.383. The reaction was then cooled to RT The mixture was washed with H2O and brine the aq. phase was extracted again with Et2O layers dried over Na2SO4 filtered concentrated in vacuo The crude product was purified by flash chromatography (SiO2, Hexane to Hexane/AcOEt 4:1)

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

実験手順: 1-(bromomethyl)-3-chloro-2-methoxybenzene. A mixture of 4-chloro-2-methoxy-1-methylbenzene (26.5 g, 169 mmol), NBS (33.1 g, 186 mmol) and benzoyl peroxide (200 mg, 0.826 mmol) in CHCl3 was heated to reflux for 24 h. The reaction was allowed to cool to RT and then concentrated in vacuo. The residue was stirred with petroleum ether and the resulting suspension was filtered off and the filtrate was concentrated in vacuo to give the title compound (30.9 g) as brown oil, which was used as it is in the next step. UPLC (2 min) rt 1.708 min. was heated to reflux for 24 h concentrated in vacuo the resulting suspension was filtered off the filtrate was concentrated in vacuo

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

実験手順: 2-(3-chloro-2-methoxyphenyl)acetonitrile. A solution of 1-(bromomethyl)-3-chloro-2-methoxybenzene (30.8 g, 131 mmol) in EtOH (150 mL) at RT and under N2 was treated with an aq. solution of NaCN (12.8 g, 262 mmol in 50 mL H2O) and the mixture was heated to 100° C. for 3 h. The reaction was then cooled to RT and taken up in Et2O. The mixture was washed with H2O and brine, and the aq. phase was extracted again with Et2O. The combined org. layers dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, Hexane to Hexane/AcOEt 4:1) to afford the title compound (15.8 g) as brown oil. UPLC (2 min) rt 1.383. The reaction was then cooled to RT The mixture was washed with H2O and brine the aq. phase was extracted again with Et2O layers dried over Na2SO4 filtered concentrated in vacuo The crude product was purified by flash chromatography (SiO2, Hexane to Hexane/AcOEt 4:1)

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

実験手順: 1-(bromomethyl)-3-chloro-2-methoxybenzene. A mixture of 4-chloro-2-methoxy-1-methylbenzene (26.5 g, 169 mmol), NBS (33.1 g, 186 mmol) and benzoyl peroxide (200 mg, 0.826 mmol) in CHCl3 was heated to reflux for 24 h. The reaction was allowed to cool to RT and then concentrated in vacuo. The residue was stirred with petroleum ether and the resulting suspension was filtered off and the filtrate was concentrated in vacuo to give the title compound (30.9 g) as brown oil, which was used as it is in the next step. UPLC (2 min) rt 1.708 min. was heated to reflux for 24 h concentrated in vacuo the resulting suspension was filtered off the filtrate was concentrated in vacuo

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

実験手順: 1-(bromomethyl)-3-chloro-2-methoxybenzene. A mixture of 4-chloro-2-methoxy-1-methylbenzene (26.5 g, 169 mmol), NBS (33.1 g, 186 mmol) and benzoyl peroxide (200 mg, 0.826 mmol) in CHCl3 was heated to reflux for 24 h. The reaction was allowed to cool to RT and then concentrated in vacuo. The residue was stirred with petroleum ether and the resulting suspension was filtered off and the filtrate was concentrated in vacuo to give the title compound (30.9 g) as brown oil, which was used as it is in the next step. UPLC (2 min) rt 1.708 min. was heated to reflux for 24 h concentrated in vacuo the resulting suspension was filtered off the filtrate was concentrated in vacuo

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: A solution of 1-chloro-2-methoxy-3-methyl-benzene (13.40 g, 85.60 mmol), NBS (15.30 g, 86.00 mmol) and a catalytic amount of benzoyl peroxide (150 mg) in CCl4 was refluxed for 30 minutes. The reaction mixture was cooled to room temperature and filtered. The precipitate was washed with pentane. The solvent was distilled off and the residue was purified by column chromatography using pentane as the eluant to afford the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 4.00 (s, 3H), 4.56 (s, 2H), 7.04 (t, J=7.62 Hz, 1H), 7.29 (dd, J=7.62 Hz, 1H), 7.34 (dd, J=7.92 Hz, 1H). filtered The precipitate was washed with pentane The solvent was distilled off the residue was purified by column chromatography

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

実験手順: 2-(3-chloro-2-methoxyphenyl)acetonitrile. A solution of 1-(bromomethyl)-3-chloro-2-methoxybenzene (30.8 g, 131 mmol) in EtOH (150 mL) at RT and under N2 was treated with an aq. solution of NaCN (12.8 g, 262 mmol in 50 mL H2O) and the mixture was heated to 100° C. for 3 h. The reaction was then cooled to RT and taken up in Et2O. The mixture was washed with H2O and brine, and the aq. phase was extracted again with Et2O. The combined org. layers dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, Hexane to Hexane/AcOEt 4:1) to afford the title compound (15.8 g) as brown oil. UPLC (2 min) rt 1.383. The reaction was then cooled to RT The mixture was washed with H2O and brine the aq. phase was extracted again with Et2O layers dried over Na2SO4 filtered concentrated in vacuo The crude product was purified by flash chromatography (SiO2, Hexane to Hexane/AcOEt 4:1)

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

実験手順: 1-(bromomethyl)-3-chloro-2-methoxybenzene. A mixture of 4-chloro-2-methoxy-1-methylbenzene (26.5 g, 169 mmol), NBS (33.1 g, 186 mmol) and benzoyl peroxide (200 mg, 0.826 mmol) in CHCl3 was heated to reflux for 24 h. The reaction was allowed to cool to RT and then concentrated in vacuo. The residue was stirred with petroleum ether and the resulting suspension was filtered off and the filtrate was concentrated in vacuo to give the title compound (30.9 g) as brown oil, which was used as it is in the next step. UPLC (2 min) rt 1.708 min. was heated to reflux for 24 h concentrated in vacuo the resulting suspension was filtered off the filtrate was concentrated in vacuo

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

実験手順: 2-(3-chloro-2-methoxyphenyl)acetonitrile. A solution of 1-(bromomethyl)-3-chloro-2-methoxybenzene (30.8 g, 131 mmol) in EtOH (150 mL) at RT and under N2 was treated with an aq. solution of NaCN (12.8 g, 262 mmol in 50 mL H2O) and the mixture was heated to 100° C. for 3 h. The reaction was then cooled to RT and taken up in Et2O. The mixture was washed with H2O and brine, and the aq. phase was extracted again with Et2O. The combined org. layers dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, Hexane to Hexane/AcOEt 4:1) to afford the title compound (15.8 g) as brown oil. UPLC (2 min) rt 1.383. The reaction was then cooled to RT The mixture was washed with H2O and brine the aq. phase was extracted again with Et2O layers dried over Na2SO4 filtered concentrated in vacuo The crude product was purified by flash chromatography (SiO2, Hexane to Hexane/AcOEt 4:1)