Potassium Carbonate → Ethyl (2E)-4-(5-bromo-2-nitrophenoxy)but-2-enoate

5-Bromo-2-nitrophenol (10 g, 45.9 mmol) and K2CO3 (8.24 g, 59.6 mmol) were suspended in NMP (81 mL) (a bright red suspension) and ethyl 4-bromocrotonate (10.26 mL, 59.63 mmol) was added dropwise at room temperature. The reaction was stirred at room temperature over night (20 h). The mixture was poured into ice/water (500 mL) and stirred for 30 min. The precipitate was collected by filtration and washed with water (2×200 mL), air dried for 10 min and then washed with heptane (200 mL). Heptane (200 mL) was added to the solid and stirred for 1 h. The solid was filtered off, washed with heptane (2×50 mL) and dried in vacuo to afford a beige solid. The title compound (15.0 g, 99%) was obtained and was used without further purification.

1. additionwas added dropwise at room temperature
2. stirringstirred for 30 min
3. filtrationThe precipitate was collected by filtration
4. washwashed with water (2×200 mL), air
5. customdried for 10 min
6. washwashed with heptane (200 mL)
7. additionHeptane (200 mL) was added to the solid
8. stirringstirred for 1 h
9. filtrationThe solid was filtered off
10. washwashed with heptane (2×50 mL)
11. customdried in vacuo
12. customto afford a beige solid

ORD record

ord-0fa0ccfe2a234a8e9979fc65f6f0fb09

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394291B2