Potassium Carbonate → 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde

Temperature

0 °C

4-Difluoromethoxy-3-hydroxybenzaldehyde (10 g, 52.8 mmol) was dissolved in tetrahydrofuran (100 ml) added with potassium carbonate (44 g, 105 mmol), cooled to 0° C. and added with a solution of bromomethylcyclopropane (11 ml, 116.6 mmol) in tetrahydrofuran (50 ml). The reaction mixture was heated to reflux under stirring for 7 hrs, then fresh bromomethylcyclopropane (5.5 ml, 58.3 mmol) was added and the heating continued for further 7 hrs. The solvent was removed by vacuum distillation, then the mixture was added with 2 N sodium hydroxide (100 ml) and extracted with dichloromethane (2×100 ml). The combined organic layers were dried over sodium sulphate (5 g) and the solvent removed under reduced pressure to afford 3-cyclopropylmethoxy-4-difluoromethoxybenzaldehyde (12 g, 50 mmol, 97% yield), that was used without further purification.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux
3. waitthe heating continued for further 7 hrs
4. customThe solvent was removed by vacuum distillation
5. additionthe mixture was added with 2 N sodium hydroxide (100 ml)
6. extractionextracted with dichloromethane (2×100 ml)
7. dry with materialThe combined organic layers were dried over sodium sulphate (5 g)
8. customthe solvent removed under reduced pressure

ORD record

ord-c048088f71ce4c1e8869a792dece159a

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07671066B2