3-bromo-2-tert-butylsulfanylbenzaldehyde

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:67.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-bromo-2-tert-butylsulfanyl-benzaldehyde (6.7 g, 25 mmol) and hydroxylamine hydrochloride (7.9 g, 116 mmol) in 2-propanol (200 mL) and water (40 mL) was heated to 65-70° C. overnight. 2-Propanol was evaporated and water (150 mL) was added to the residue followed by saturated aqueous sodium bicarbonate to bring the pH to ˜8.5. The mixture was extracted with DCM (3×80 mL). The combined organic fractions were dried over sodium sulfate, filtered, and concentrated to afford the title compound, which was used immediately without further purification. 1H NMR (300 MHz, CD3OD): δ 1.28 (s, 9H), 7.25-7.35 (t, J=7.8 Hz, 1H), 7.79 (d, J=6.6 Hz, 1H), 7.89 (d, J=6.3 Hz, 1H), 8.83 (s, 1H). 2-Propanol was evaporated water (150 mL) was added to the residue The mixture was extracted with DCM (3×80 mL) The combined organic fractions were dried over sodium sulfate filtered concentrated

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-bromo-2-fluorobenzaldehyde (5.0 g, 25 mmol), potassium carbonate (4.0 g, 30 mmol) and 2-methyl-2-propanethiol (5.5 mL, 49 mmol) in dry DMF (25 mL) was heated to 110° C. in a sealed tube for 16 h. The reaction mixture was cooled to RT, added to water (100 mL) and extracted with DCM (3×50 mL). The combined organic fractions were washed with water (50 mL), dried, and evaporated to afford 6.7 g (98%) of the crude title compound which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 1.31 (s, 9H), 7.26-7.41 (m, 1H), 7.93-7.99 (m, 2H), 10.73 (s, 1H). The reaction mixture was cooled to RT extracted with DCM (3×50 mL) The combined organic fractions were washed with water (50 mL) dried evaporated

反应条件: temp:67.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-bromo-2-tert-butylsulfanyl-benzaldehyde (6.7 g, 25 mmol) and hydroxylamine hydrochloride (7.9 g, 116 mmol) in 2-propanol (200 mL) and water (40 mL) was heated to 65-70° C. overnight. 2-Propanol was evaporated and water (150 mL) was added to the residue followed by saturated aqueous sodium bicarbonate to bring the pH to ˜8.5. The mixture was extracted with DCM (3×80 mL). The combined organic fractions were dried over sodium sulfate, filtered, and concentrated to afford the title compound, which was used immediately without further purification. 1H NMR (300 MHz, CD3OD): δ 1.28 (s, 9H), 7.25-7.35 (t, J=7.8 Hz, 1H), 7.79 (d, J=6.6 Hz, 1H), 7.89 (d, J=6.3 Hz, 1H), 8.83 (s, 1H). 2-Propanol was evaporated water (150 mL) was added to the residue The mixture was extracted with DCM (3×80 mL) The combined organic fractions were dried over sodium sulfate filtered concentrated

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-bromo-2-fluorobenzaldehyde (5.0 g, 25 mmol), potassium carbonate (4.0 g, 30 mmol) and 2-methyl-2-propanethiol (5.5 mL, 49 mmol) in dry DMF (25 mL) was heated to 110° C. in a sealed tube for 16 h. The reaction mixture was cooled to RT, added to water (100 mL) and extracted with DCM (3×50 mL). The combined organic fractions were washed with water (50 mL), dried, and evaporated to afford 6.7 g (98%) of the crude title compound which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 1.31 (s, 9H), 7.26-7.41 (m, 1H), 7.93-7.99 (m, 2H), 10.73 (s, 1H). The reaction mixture was cooled to RT extracted with DCM (3×50 mL) The combined organic fractions were washed with water (50 mL) dried evaporated

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-bromo-2-fluorobenzaldehyde (5.0 g, 25 mmol), potassium carbonate (4.0 g, 30 mmol) and 2-methyl-2-propanethiol (5.5 mL, 49 mmol) in dry DMF (25 mL) was heated to 110° C. in a sealed tube for 16 h. The reaction mixture was cooled to RT, added to water (100 mL) and extracted with DCM (3×50 mL). The combined organic fractions were washed with water (50 mL), dried, and evaporated to afford 6.7 g (98%) of the crude title compound which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 1.31 (s, 9H), 7.26-7.41 (m, 1H), 7.93-7.99 (m, 2H), 10.73 (s, 1H). The reaction mixture was cooled to RT extracted with DCM (3×50 mL) The combined organic fractions were washed with water (50 mL) dried evaporated

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:67.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-bromo-2-tert-butylsulfanyl-benzaldehyde (6.7 g, 25 mmol) and hydroxylamine hydrochloride (7.9 g, 116 mmol) in 2-propanol (200 mL) and water (40 mL) was heated to 65-70° C. overnight. 2-Propanol was evaporated and water (150 mL) was added to the residue followed by saturated aqueous sodium bicarbonate to bring the pH to ˜8.5. The mixture was extracted with DCM (3×80 mL). The combined organic fractions were dried over sodium sulfate, filtered, and concentrated to afford the title compound, which was used immediately without further purification. 1H NMR (300 MHz, CD3OD): δ 1.28 (s, 9H), 7.25-7.35 (t, J=7.8 Hz, 1H), 7.79 (d, J=6.6 Hz, 1H), 7.89 (d, J=6.3 Hz, 1H), 8.83 (s, 1H). 2-Propanol was evaporated water (150 mL) was added to the residue The mixture was extracted with DCM (3×80 mL) The combined organic fractions were dried over sodium sulfate filtered concentrated

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-bromo-2-fluorobenzaldehyde (5.0 g, 25 mmol), potassium carbonate (4.0 g, 30 mmol) and 2-methyl-2-propanethiol (5.5 mL, 49 mmol) in dry DMF (25 mL) was heated to 110° C. in a sealed tube for 16 h. The reaction mixture was cooled to RT, added to water (100 mL) and extracted with DCM (3×50 mL). The combined organic fractions were washed with water (50 mL), dried, and evaporated to afford 6.7 g (98%) of the crude title compound which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 1.31 (s, 9H), 7.26-7.41 (m, 1H), 7.93-7.99 (m, 2H), 10.73 (s, 1H). The reaction mixture was cooled to RT extracted with DCM (3×50 mL) The combined organic fractions were washed with water (50 mL) dried evaporated