Hydrochloric Acid → 3-(4-Chlorophenyl)prop-2-enal

Temperature

90 °C

To a stirred solution of 1-chloro-4-iodobenzene (2 g, 8.39 mmol) in DMF (30 mL) were added acrolein diethyl acetal (3.84 mL, 8.39 mmol), n-Bu4NOAc (5.06 g, 16.8 mmol), K2CO3 (1.74 g, 12.6 mmol), KCl (0.63 g, 8.39 mmol) and Pd(OAc)2 (0.056 g, 0.25 mmol). The mixture was stirred for 1.5 hour at 90° C. After cooling, 2 N HCl was slowly added and the reaction mixture was stirred at room temperature for 10 minutes. Subsequently, it was diluted with ether (200 mL) and washed with water (200 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (n-hexane/ethyl acetate mixture in a volume ratio 8:2) to give intermediate 5d (74% yield) which was characterised as follows:

1. temperatureAfter cooling
2. stirringthe reaction mixture was stirred at room temperature for 10 minutes
3. washwashed with water (200 mL)
4. dry with materialThe organic layer was dried over MgSO4
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by flash chromatography (n-hexane/ethyl acetate mixture in a volume ratio 8:2)

ORD record

ord-112850282b7444beb9b9e26b18590c1d

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07638505B2