2,3,4,5-Tetrafluorobenzoyl chloride → Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate

Potassium ethyl malonate (3.66 g, 21.5 mmol), MgCl2 (2.44 g, 25.7 mmol) and TEA (2.05 g, 20.3 mmol) were mixed in acetonitrile (70 ml) at 10-15° C. for 2.5 hr. 2,3,4,5-tetrafluorobenzoyl chloride (2.00 g, 10.3 mmol) in acetonitrile (10 ml) was added at 0° C. over 15 min followed by a second addition of TEA (0.23 g, 2.3 mmol). After allowing to warm to RT, the mixture was stirred for 16 hr. After removal of volatiles in vaccuo Toluene (30 ml) was added and removed in vacuo. Following the addition of toluene (60 ml), HCl 1.5 M (40 ml) was added cautiously, ensuring the temperature did not exceed 25° C. The organic fraction was washed with HCl 1.5 M (2×25 ml) and water (2×25 ml), dried over MgSO4 and reduced to a light orange oil in vacuo ([M+1]+ 265, 98%).

1. customAfter removal of volatiles in vaccuo Toluene (30 ml)
2. additionwas added
3. customremoved in vacuo
4. additionthe addition of toluene (60 ml), HCl 1.5 M (40 ml)
5. additionwas added cautiously
6. customdid not exceed 25° C
7. washThe organic fraction was washed with HCl 1.5 M (2×25 ml) and water (2×25 ml)
8. dry with materialdried over MgSO4

ORD record

ord-2465959bad2f43f79221100ebc3c25ae

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612063B2