Pyridine → 1-[3-Bromoprop-1-enyl]-4-methoxy-2-nitrobenzene

To a stirred slurry of triphenyl phosphine (16.4 g, 0.627 mol) in dry DCM (150 mL) under nitrogen at 0° C., is added dropwise a solution of bromine (3.2 mL, 0.0627 mol) in DCM (30 mL). After stirring for 15 min, a solution of (2E)-3-(4-methoxy-2-nitrophenyl)prop-2-en-1-ol (10 g, 0.044 mol) in dry DCM (100 mL) is added dropwise to the reaction mixture followed by a dropwise addition of pyridine (5.05 mL, 0.06 mol) at 0° C. After stirring at room temperature for another 4 h, the reaction mixture is quenched with ice and the product extracted with DCM. The organic layer is washed with water then brine and dried over Na2SO4. The solvent is removed under reduced pressure and the residue is purified by chromatography using silica-gel (60-120 mesh) and petrol ether/EtOAc as eluent to afford (7 g, 53%) of the title compound as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 7.52-7.55 (m, 1H), 7.42-7.47 (m, 1H), 7.11-7.16 (m, 1H), 7.06-7.09 (m, 1H), 6.23-6.29 (m, 1H), 4.15-4.18 (m, 2H), 3.88 (s, 3H).

1. stirringAfter stirring at room temperature for another 4 h
2. customthe reaction mixture is quenched with ice
3. extractionthe product extracted with DCM
4. washThe organic layer is washed with water
5. dry with materialbrine and dried over Na2SO4
6. customThe solvent is removed under reduced pressure
7. customthe residue is purified by chromatography

ORD record

ord-f72834f0ea1f4fe2bfeae17a86224ba8

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08614215B2