Hydrochloric Acid → 26431-60-7

Temperature

-78 °C

A mixture of 2-bromomethyl-4-trifluoromethyl-furan (500 mg, 3.57 mmol), hexamethylenetetramine (HMTA) (637 mg, 4.54 mmol) and water (2.6 mL) were placed in a 50 mL pear-shaped flask equipped with a vigreaux column atop of which is attached to dry-ice condenser chilled at −78° C. The mixture was heated at reflux for 1 h, and then treated with concentrated HCl (1.7 mL). Reflux was maintained for an additional 1 h before the reaction was cooled to rt, diluted with water and extracted with DCM (4×50 mL). The combined organic extracts were washed with water, brine, dried (Na2SO4) and carefully concentrated to give 4-(trifluoromethyl)furan-2-carbaldehyde. 1H NMR (400 MHz, CDCl3) δ ppm 7.37 (m, 1H), 8.01 (m, 1H), 9.74 (d, J=0.54 Hz, 1H).

1. customwere placed in a 50 mL pear-shaped flask
2. customequipped with a vigreaux column atop of which
3. customis attached to dry-ice condenser
4. temperatureThe mixture was heated
5. temperatureat reflux for 1 h
6. temperatureReflux
7. temperaturewas maintained for an additional 1 h before the reaction
8. temperaturewas cooled to rt
9. extractionextracted with DCM (4×50 mL)
10. washThe combined organic extracts were washed with water, brine
11. dry with materialdried (Na2SO4)
12. concentrationcarefully concentrated

ORD record

ord-1b5155d7e58140ae88f2d87ce0f49f03

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07884124B2