4-Chloro-2-nitrophenol → HCID 22997608, compound

Participants

Reaction Steps

A mixture of 4-chloro-2-nitrophenol (100 g), allyl bromide (69.7 g), and potassium carbonate (95.5 g) in acetone (1 L) was refluxed for 6 hours. After cooling to room temperature and filtration, the filtrate was concentrated to give a residue. The residue was extracted with dichloromethane. The organic layer was washed with water, dried over MgSO4, and concentrated in vacuo to give a crude product (110.9 g, 90%) which was used in the next step without purification. 42 g of the crude product was heated at 180° C. for 8 hours. Purification by flash chromatography over silica gel (elution with 50% ethyl acetate in hexanes) gave 22 g (50%) of 2-nitro-4-chloro-6-allylphenol. 1H NMR (300 MHz, CDCl3) δ8.00 (d, J=2.6 Hz, 1 H), 7.44 (d, J=2.6 Hz, 1 H), 6.00-5.89 (m, 1 H), 5.20-5.12 (m, 2 H), 3.48 (d, J=6.69 Hz, 2 H).

Provenance & Evidence