Potassium Carbonate → HCID 60650934, compound

Temperature

70 °C

To a stirred solution of 4-cyano phenol (1 g, 8.4 mmol) in acetone (15 ml) was added K2CO3 (3.48 g, 25.0 mmol), followed by 4-iodobenzyl bromide (2.7 g, 9.2 mmol) at 20-35° C. and the reaction mixture was stirred at 70° 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 5% ethyl acetate/hexane as an eluent to get the desired compound as a white solid (700 mg, 35%). 1H NMR (400 MHz, DMSO-d6) δ 7.80-7.75 (m, 4H), 7.26 (d, J=8.3 Hz, 2H), 7.19-7.15 (m, 2H), 5.18 (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 5% ethyl acetate/hexane as an eluent

ORD record

ord-d369fb3f851c40708f5f4c4c03e40751

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062002B2