Dichloromethane → 2-Chloro-3,4,5,6-tetramethoxybenzaldehyde

HRID 1527672Notes

Reaction equation

HRID 1527672 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[C:8]([O:15][CH3:16])=[CH:7][C:4]=1[CH:5]=[O:6].C(Cl)[Cl:18]>>[Cl:18][C:7]1[C:8]([O:15][CH3:16])=[C:9]([O:13][CH3:14])[C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[C:4]=1[CH:5]=[O:6]

Participants

3

Reactant 2

HCID 6344Dichloromethane2×HCID 6394122,3,4,5-Tetramethoxybenzaldehyde

Product 1

HCID 461798872-Chloro-3,4,5,6-tetramethoxybenzaldehydeYield 97%

Procedure

According to a general aryl chlorination procedure by Lopez-Alvarado,39 19 (0.767 g, 3.39 mmol) was dissolved in CH2Cl2 (10.0 mL) at room temperature and then SO2Cl2 (neat, 0.31 mL, 3.7 mmol) was added at room temperature. The reaction was stirred for 1 hour and monitored by 1H NMR for completion. The reaction was then diluted with CH2Cl2, washed with brine, dried over MgSO4, filtered, and condensed. The resulting oil was then purified by flash column chromatography (1:4 Et2O:hexanes) to provide 20 (0.861 g, 3.30 mmol, 97%) as a colorless oil.

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customcondensed
  5. customThe resulting oil was then purified by flash column chromatography (1:4 Et2O:hexanes)

Sources & evidence

ORD record
ord-5c7bfab050e24190949009acdbd8cfe8
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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