HCID 24851925, compound → HCID 68767239, compound

To a solution of 1.5 g of 4-acetyl-3-chlorobenzonitrile in 25 ml anhydrous THF is added 158 mg sodium boron hybrid at 0° C. The ice bath is removed and the reaction mixture is stirred for 18 h at room temperature. The reaction mixture is poured into 90 ml of 1N aqueous HCl solution. The aqueous layer is extracted with ethyl acetate (3×50 ml). The combined organic layers are washed with a saturated solution of sodium chloride (100 ml), dried over MgSO4 and evaporated to dryness under reduced pressure. The remaining residue is purified by flash chromatography (n-hexane/ethyl acetate, 6/4 (v/v)) to yield the title compound.

1. customThe ice bath is removed
2. additionThe reaction mixture is poured into 90 ml of 1N aqueous HCl solution
3. extractionThe aqueous layer is extracted with ethyl acetate (3×50 ml)
4. washThe combined organic layers are washed with a saturated solution of sodium chloride (100 ml)
5. dry with materialdried over MgSO4
6. customevaporated to dryness under reduced pressure
7. customThe remaining residue is purified by flash chromatography (n-hexane/ethyl acetate, 6/4 (v/v))

ORD record

ord-b94d0f15a8d64573a27885ee1f9d833d

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273890B2