Cesium carbonate → Methyl 3-(3,4-dichlorophenyl)prop-2-enoate

Cool a solution of 3-(3,4-dichlorophenyl)-2-propeneoic acid (100 g, 461 mmol) in dry DMF (500 mL) to 0° C. and treat with Cs2CO3 (100 g, 307 mmol, 0.66 eq). Stir the resulting off-white slurry for 15 min, then add CH3 l (33 mL, 530 mmol, 1.15 eq) via syringe. After 1 h, add additional DMF (250 mL), stir the slurry for 14 h and partition between EtOAc (1.5 L) and half saturated aqueous NaHCO3 (500 mL). Separate the organic layer and extract the aqueous layer twice with EtOAc (1 L, 500 mL). Wash the combined organic layers with half saturated aqueous NaHCO3 (500 mL) and water (5×500 mL), then dry (Na2SO4) and concentrate to obtain 105.4 g (456 mmol, 99%) of methyl 3-(3,4-dichlorophenyl)-2-propenoate as light brown needles.

1. waitAfter 1 h
2. stirringstir the slurry for 14 h
3. custompartition between EtOAc (1.5 L) and half saturated aqueous NaHCO3 (500 mL)
4. customSeparate the organic layer
5. extractionextract the aqueous layer twice with EtOAc (1 L, 500 mL)
6. washWash the combined organic layers with half saturated aqueous NaHCO3 (500 mL) and water (5×500 mL)
7. dry with materialdry (Na2SO4)
8. concentrationconcentrate

ORD record

ord-04ca80a7a1e54cf5be00bde1e4f2c695

Source dataset

uspto-grants-1998_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05789422