Tetrahydrofuran → Ethyl trans-4-Bromocinnamate

A solution of triethyl phosphonoacetate (13.1 g, 0.0589 mol) was added slowly (dropwise) to a solution of Potassium-tert-butoxide (6.59 g, 0.0589 mol), in dry THF (150 mL) at −5° C., stirred for 30-45 mins at the same temperature, then a solution of 4-Bromo benzaldehyde (10 g, 0.054 mol), in dry THF (50 mL) was slowly added dropwise at −5° C. over a period of 15 mins, stirred the reaction mixture for 30 mins at the same temperature. After completion of reaction by TLC, the reaction mixture was poured into ice water (300 mL), extracted with EtOAc (2×200 mL). The combined organic extracts were washed with sat NaHCO3 solution (200 mL), water (200 mL), brine (200 mL) and dried over anhydrous Na2SO4, filtered and evaporated to get crude (E)-ethyl 3-(4-bromophenyl)acrylate (10 g, 72%) as pale green liquid. This is carried to next step without further purification.

1. customAfter completion of reaction by TLC
2. extractionextracted with EtOAc (2×200 mL)
3. washThe combined organic extracts were washed with sat NaHCO3 solution (200 mL), water (200 mL), brine (200 mL)
4. dry with materialdried over anhydrous Na2SO4
5. filtrationfiltered
6. customevaporated

ORD record

ord-1be8ea45632c4145a70f84f615b51d27

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006449B2