Dimethylformamide → 3-Chloro-5-methoxybenzaldehyde

Temperature

0 °C

3,5-Dichloroanisole (74.0 g, 419 mmol) in THF (200 mL) was added dropwise to magnesium metal (14.2 g, 585 mmol, pre-washed with 0.5 N HCl) in THF (100 mL) at 25° C. After the addition, 1,2-dibromoethane (3.9 g, 20.8 mmol) was added dropwise. The resultant dark brown mixture was heated at reflux for 3 h. The mixture was cooled to 0° C., and N,N-dimethylformamide (60 mL) was added in one portion. The mixture was partitioned with diethyl ether (3×400 mL) and 6N HCl (500 mL). The combined organic extracts were washed with brine (300 mL), dried (Na2SO4), filtered and concentrated in vacuo to give an oil. Flash chromatography (2×) on silica gel eluting with Hex:EtOAc (4:1) afforded the sub-title compound (38.9 g, 54%/) as a yellow oil.

1. additionwas added dropwise
2. temperatureThe resultant dark brown mixture was heated
3. temperatureat reflux for 3 h
4. customThe mixture was partitioned with diethyl ether (3×400 mL) and 6N HCl (500 mL)
5. washThe combined organic extracts were washed with brine (300 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give an oil

ORD record

ord-3c16a7f0c46742808877c6222350da3d

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07129233B2