Bromobenzene → 3,5-Dimethyl-N-phenylaniline

온도

175 °C

A mixture of 9.6 g (58.8 mmole) of N-acetyl-3,5-dimethylaniline, 8.13 g (58.8 mmole) of potassium carbonate (dried at 155° C. under vacuum), 23 g (147 mmole) of bromobenzene (dried over molecular sieves), and 1.12 g (5.9 mmole) of cuprous iodide was heated in a 175° C. oil bath under a reflux condenser under nitrogen for 18 hours. The mixture was cooled to room temperature and triturated with 1 liter of benzene. The solution was concentrated in vacuo. The residue was treated with 60 mL of EtOH and 7.76 g (118 mmole) of potassium hydroxide and the resulting mixture was heated to reflux for two hours. The mixture was cooled and the solvent removed in vacuo. The residue was taken up in 150 mL of hexanes and 20 mL of EtOAc and the resulting solution was washed with 2×100 mL of 2N aqueous HCl and 60 mL of water. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on 210 g of silica gel with 2 liters of 3:1 hexanes CH2Cl2 to give 5.5 g (47%) of a light red oil.

1. temperatureThe mixture was cooled to room temperature
2. customtriturated with 1 liter of benzene
3. concentrationThe solution was concentrated in vacuo
4. temperaturethe resulting mixture was heated
5. temperatureto reflux for two hours
6. temperatureThe mixture was cooled
7. customthe solvent removed in vacuo
8. wash20 mL of EtOAc and the resulting solution was washed with 2×100 mL of 2N aqueous HCl and 60 mL of water
9. dry with materialThe organic layer was dried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe residue was purified by flash chromatography on 210 g of silica gel with 2 liters of 3:1 hexanes CH2Cl2

ORD 기록

ord-c45e5858996c436c95f2c9efb4128c0b

출처 데이터셋

uspto-grants-1994_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05348955