Dimethylformamide → 2,3-Dichloro-6-methoxy-benzaldehyde

Temperature

-70 °C

3,4-Dichloroanisole (12.5 g, 70.6 mmol) was dissolved in tetrahydrofuran (130 ml) and cooled to −76° C. n-Butyllithium (31 ml of 2.5 molar in hexanes, 77.7 mmol) was added dropwise keeping the temperature below −70° C. The solution was stirred at −70° C. for 30 minutes, then dimethylformamide (6.0 ml, 77.7 mmol) was added dropwise. The mixture was allowed to warm up to room temperature and was then poured onto ice (500 ml) and extracted with diethyl ether. The ether extracts were washed with brine then dried over anhydrous Na2SO4, filtered, and the solvent removed in vacuo to give the crude product. This material was stirred and heated to just below the reflux temperature in hexane (100 ml) and dichloromethane (5 ml), then cooled, and the solid filtered off to give the title compound as an off-white powder (10.0 g).

1. additionwas added dropwise
2. customthe temperature below −70° C
3. temperatureto warm up to room temperature
4. additionwas then poured onto ice (500 ml)
5. extractionextracted with diethyl ether
6. washThe ether extracts were washed with brine
7. dry with materialthen dried over anhydrous Na2SO4
8. filtrationfiltered
9. customthe solvent removed in vacuo
10. customto give the crude product
11. stirringThis material was stirred
12. filtrationthe solid filtered off

ORD record

ord-e880a340498845419210acb004b6c5c5

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07572797B2