4-Fluorophenylacetyl chloride → HCID 18400186, compound

Temperature

0 °C

To a suspension of 14.6 g (80 mmol) of CdCl2 in 200 mL of ether cooled to 0° C. was added 115 mL of 1.3M solution of 3-butene-1-magnesium bromide dropwise. The mixture was refluxed for 1 h and ether was then removed by distillation. Benzene (500 mL) was introduced, followed by a solution of 17.5 g (100 mmol) 4-fluorophenylacetyl chloride. After refluxing for 1 h, the reaction mixture was quenched with 200 mL of saturated aqueous NH4Cl, 50 mL of 1N HCl, and extracted with 200 mL of 1:1 hexane/EtOAC. The organic phase was dried over MgSO4 and concentrated. The residue was purified by flash chromatography eluted with 4:1 hexane/EtOAc to give 15 g of the title product.

1. temperatureThe mixture was refluxed for 1 h
2. customether was then removed by distillation
3. additionBenzene (500 mL) was introduced
4. temperatureAfter refluxing for 1 h
5. customthe reaction mixture was quenched with 200 mL of saturated aqueous NH4Cl, 50 mL of 1N HCl
6. extractionextracted with 200 mL of 1:1 hexane/EtOAC
7. dry with materialThe organic phase was dried over MgSO4
8. concentrationconcentrated
9. customThe residue was purified by flash chromatography
10. washeluted with 4:1 hexane/EtOAc

ORD record

ord-f1ae6206f82a42c9b0014d56a374b375

Source dataset

uspto-grants-1998_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05710140