Dichloromethane → 4-Bromo-2-methoxybenzonitrile

In a 1 L round-bottomed flask, 53.94 g (270 mmol) of 4-bromo-2-fluorobenzonitrile was dissolved in 500 mL of THF. Sodium methoxide (21.99 g, 407 mmol) was added and the mixture was heated to reflux until TLC (SiO2:CH2Cl2) showed complete consumption of starting material. The mixture was poured into 1N HCl and the THF was evaporated in vacuo. The remaining mixture was extracted with diethyl ether. The extract was dried (MgSO4) and filtered over a plug of silica gel. The plug was eluted with CH2Cl2 and the filtrate was evaporated in vacuo to afford 45.56 g (80%) of the product as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.42 (d, 1H), 7.17 (dd, 1H), 7.14 (d, 1H), 3.95 (s, 3H).

1. temperaturethe mixture was heated
2. customconsumption of starting material
3. additionThe mixture was poured into 1N HCl
4. customthe THF was evaporated in vacuo
5. extractionThe remaining mixture was extracted with diethyl ether
6. dry with materialThe extract was dried (MgSO4)
7. filtrationfiltered over a plug of silica gel
8. washThe plug was eluted with CH2Cl2
9. customthe filtrate was evaporated in vacuo

ORD record

ord-73ac508e60e04dd5862d71707d17da19

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07507826B2