Methanol → HCID 60702225, compound

A stirring solution of 3-bromo-4-methoxy-benzonitrile (1.00 g, 4.7 mmol) in THF (30 ml) was treated drop-wise with borane-THF (14.2 ml, 1M solution in THF, 14.2 mmol). The mixture was heated at reflux, under argon for 5 h. To the cooled reaction mixture was cautiously added MeOH (20 ml). The volatiles were removed in vacuo and the residue was treated with 2N HCl (20 ml). After heating at reflux for 0.45 h and cooling to room temperature the mixture was basified by addition of solid K2CO3. The basic solution was extracted with diethyl ether (2×). The organic phase was dried (MgSO4) and the solvent removed in vacuo to afford the title compound as a colourless oil (64%).

1. temperatureThe mixture was heated
2. temperatureat reflux, under argon for 5 h
3. customTo the cooled reaction mixture
4. customThe volatiles were removed in vacuo
5. additionthe residue was treated with 2N HCl (20 ml)
6. temperatureAfter heating
7. temperatureat reflux for 0.45 h
8. additionwas basified by addition of solid K2CO3
9. extractionThe basic solution was extracted with diethyl ether (2×)
10. dry with materialThe organic phase was dried (MgSO4)
11. customthe solvent removed in vacuo

ORD record

ord-f446c5c1f2ca4b21879adc68a053ceb4

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07078565B2