Acrylonitrile → HCID 67545352, compound

A mixture of 4-bromo-2-hydroxybenzaldehyde (20 g), acrylonitrile (26.4 g) and DABCO (0.78 g) was heated at reflux for 8 hours. After cooling, the reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was concentrated and the residue was filtered through silica gel. The 7-bromo-2H-chromene-3-carbonitrile thus obtained (7.5 g) was boiled at reflux with sodium hydroxide solution (10.2 g of sodium hydroxide in 100 ml of water) for 8 hours. The cooled reaction mixture was washed with methyl tert-butyl ether, acidified with hydrochloric acid and extracted with ethyl acetate. Concentration of the organic phase gave 7-bromo-2H-chromene-3-carboxylic acid. This acid (3.0 g) was heated to 85° C. with DPPA (3.2 g), triethylamine (1.6 ml) and toluene (30 ml) for 12 hours. Then hydrochloric acid (6 N) was added and the mixture was heated to reflux for 2 hours. The cooled reaction mixture was extracted with ethyl acetate and the organic phase was concentrated. The product was thus obtained with the molecular weight of 227.06 (C9H7BrO2); MS (ESI): 227 (M+H+).

1. temperaturewas heated
2. temperatureat reflux for 8 hours
3. temperatureAfter cooling
4. washwashed with water
5. concentrationThe organic phase was concentrated
6. filtrationthe residue was filtered through silica gel

ORD record

ord-65127f6c9aa14d1c85f22330d112d3a6

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609731B2