Dimethylformamide → 2-Bromo-4,6-dimethoxybenzaldehyde
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1.O=P(Cl)(Cl)Cl.CN([CH:20]=[O:21])C>>[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[C:7]=1[CH:20]=[O:21]Participants
4
Procedure
To a mixture of 1-bromo-3,5-dimethoxybenzene (21.7 g, 100.0 mmol) in DMF (80 mL) was added POCl3 (15 mL, 150 mmol) at 0° C. The mixture was stirred at room temperature for 30 min and then heated at 100° C. for an additional 30 min. The reaction mixture was cooled to room temperature and poured onto ice. The precipitate was collected by filtration and dried under high vacuum to give the title compound as a yellow solid. (19.4 g, Yield: 79%). 1H NMR (400 MHz, DMSO-d) δ10.18 (s, 1H), 6.91-6.91 (d, J=2.0 Hz, 1H), 6.74-6.73 (d, J=2.0 Hz, 1H), 3.90 (s, 3H), 3.89 (s, 3H).
Workup
- temperatureheated at 100° C. for an additional 30 min
- temperatureThe reaction mixture was cooled to room temperature
- additionpoured onto ice
- filtrationThe precipitate was collected by filtration
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-8eee5d84a7da42d1a212e37948fde50b
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08343944B2
Reaction notes
Loading…