Allyl bromide → 2-(Allyloxy)-4-nitrobenzonitrile

Temperature

0 °C

To a stirred solution of 2-hydroxy-4-nitrobenzonitrile (5.0 g, 30.48 mmol) in DMF (50 mL) was added Cs2CO3 (19.9 g, 60.97 mmol). The mixture was cooled to 0° C., and allyl bromide (4.39 g, 36.58 mmol) was added dropwise. The reaction mixture was stirred for 12 h at 90° C. under nitrogen. The reaction mixture was cooled to rt and concentrated to remove DMF, then EtOAc (50 mL) was added to the residue. The mixture was washed with water (2×30 mL) and brine (30 mL). The organic layer was dried with Na2SO4, and concentrated in vacuo to afford the yellow solid, 2-(allyloxy)-4-nitrobenzonitrile (4 g, 65% yield). LC-MS (M+H)+=205.2 1H NMR (400 MHz, CDCl3) δ ppm 7.87-7.86 (m, 1H), 7.811 (s, 1H), 7.76 (d, 1H, J=8.4 Hz), 6.11-6.01 (m, 1H), 5.56-5.55 (dd, 1H, J=1.6, 3.2 Hz), 5.52 (d, 1H, J=1.6 Hz), 4.79 (d, 2H, J=4.8 Hz).

1. temperatureThe reaction mixture was cooled to rt
2. concentrationconcentrated
3. customto remove DMF
4. additionEtOAc (50 mL) was added to the residue
5. washThe mixture was washed with water (2×30 mL) and brine (30 mL)
6. dry with materialThe organic layer was dried with Na2SO4
7. concentrationconcentrated in vacuo

ORD record

ord-90090286957347419308af4fb14ae1b2

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637523B2