Benzoyl chloride, 3-chloro- → HCID 58573538, compound

Temperature

-10 °C

To a solution of 3-chlorobenzoyl chloride (7 ml, 54.7 mmol) in THF (60 mL) was added copper (I) iodide (0.521 g, 2.73 mmol). The slurry was cooled to −10° C. and 3-butenylmagnesium bromide (0.5M in THF) (112 ml, 55.8 mmol) was added dropwise via cannula over 30 min. The reaction mixture was stirred at −10° C. for 1 h and then warmed to room temperature. The reaction mixture was concentrated to 25 mL and diluted with 100 mL DCM and 100 mL 1M HCl. The layers were separated and the organic layer was filtered. The filtrate was washed with sat. NaHCO3, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent: 0 to 50% DCM in hexanes) to give the title compound.

1. temperaturewarmed to room temperature
2. concentrationThe reaction mixture was concentrated to 25 mL
3. additiondiluted with 100 mL DCM and 100 mL 1M HCl
4. customThe layers were separated
5. filtrationthe organic layer was filtered
6. washThe filtrate was washed with sat. NaHCO3
7. dry with materialdried over Na2SO4
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by flash chromatography on silica gel (eluent: 0 to 50% DCM in hexanes)

ORD record

ord-6ed0c3152cd24be1b32f43f0936d8fd8

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296736B2