4-Iodophenol → 2-(4-Iodophenoxy)acetonitrile

温度

80 °C

To a stirred solution of 4-iodo phenol (700 mg, 3.1 mmol) in acetonitrile (7 ml) was added K2CO3 (1.31 g, 9.5 mmol), followed by bromo acetonitrile (410 mg, 3.4 mmol) at 20-35° C. and the reaction mixture was stirred at 80° C. for 6 h. The progress of the reaction was monitored by TLC. After 6 h of stirring, the mixture was cooled to 20-35° C., diluted with water (50 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with brine (50 ml), followed by drying over anhydrous Na2SO4 and filtering. The filtrate was rotary evaporated to get residue which was purified by column chromatography using a mixture of 15% ethyl acetate/hexane as an eluent to get the desired compound as a pale yellow liquid (400 mg, 51%). 1H NMR (400 MHz, DMSO-d6) δ 7.65 (dt, J=5.4, 2.9 Hz, 2H), 6.79-6.77 (m, 2H), 4.74 (s, 2H).

1. stirringAfter 6 h of stirring
2. temperaturethe mixture was cooled to 20-35° C.
3. extractionextracted with ethyl acetate (2×50 ml)
4. washThe combined organic layers were washed with brine (50 ml)
5. dry with materialby drying over anhydrous Na2SO4
6. filtrationfiltering
7. customThe filtrate was rotary evaporated
8. customto get residue which
9. customwas purified by column chromatography
10. additiona mixture of 15% ethyl acetate/hexane as an eluent

ORDレコード

ord-a370c0a20d494e77a3803f9374a81ca2

出典データセット

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09062002B2