Hydrochloric Acid → 2-Chloro-4-formyl-3-methylbenzonitrile

Temperature

-32 °C

A mixture of 2-chloro-4-iodo-3-methylbenzonitrile (150 g, 0.54 mol) and THF (1200 ml) was cooled down to −32° C. A 2 M i-PrMgCl-THF-solution (541 ml, 1.08 mol) was added slowly during 1 h and the mixture was stirred at −32° C. for 2 h. DMF (83 ml, 1.08 mol) was added at −32° C. and the reaction mixture was allowed to warm to RT. After stirring overnight 10% HCl solution (1000 ml) was added at 0° C. The layers were separated and the aqueous layer was extracted with diethyl ether (2×900 ml). The combined organic layers were washed with saturated NaHCO3 solution (900 ml) and brine (750 ml). The organic layer was dried with Na2CO4, filtered and evaporated. The dried crude product (95 g) was treated with hot n-heptane and activated carbon. The title compound was obtained as a yellow solid and used without further purification. 1H-NMR (400 MHz; CDCl3): δ 2.78 (s, 3H), 7.71 (d, 1H), 7.84 (d, 1H), 10.36 (s, 1H).

1. temperatureto warm to RT
2. additionwas added at 0° C
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with diethyl ether (2×900 ml)
5. washThe combined organic layers were washed with saturated NaHCO3 solution (900 ml) and brine (750 ml)
6. dry with materialThe organic layer was dried with Na2CO4
7. filtrationfiltered
8. customevaporated
9. dry with materialThe dried crude product (95 g)
10. additionwas treated with hot n-heptane and activated carbon

ORD record

ord-c597f9dc0d62454c9d70a791782d5897

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08975254B2