Dimethylformamide → 2-Bromo-4,6-dimethoxybenzaldehyde

HRID 1798106Notes

Reaction equation

HRID 1798106 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

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 6391871-Bromo-3,5-dimethoxybenzene

Product 1

HCID 114023032-Bromo-4,6-dimethoxybenzaldehydeYield 79%

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 reaction mixture was stirred at room temperature for 30 min and then heated to 100° C. for an additional 30 min. After cooling to room temperature, the mixture was poured onto ice (200 g). 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, CDCl3) δ 12.33 (s, 1H), 10.11 (s, 1H), 6.47 (s, 1H), 6.39 (s, 1H), 5.49 (t, J=3.13 Hz, 1H), 3.78-3.90 (m, 1H), 3.52-3.72 (m, 1H), 2.54 (s, 3H), 1.77-2.03 (m, 3H), 1.53-1.70 (m, 3H); MS (ESI) m/z=285 [M+H]+.

Workup

  1. temperatureheated to 100° C. for an additional 30 min
  2. temperatureAfter cooling to room temperature
  3. additionthe mixture was poured onto ice (200 g)
  4. filtrationThe precipitate was collected by filtration
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-c4c2df0bf37c4a70adcc94e1121d8901
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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