Dimethyl Sulfate → 5-Bromo-2-chloro-3,4-dimethoxybenzaldehyde

HRID 576383Notes

Reaction equation

HRID 576383 reaction equation
[Br:1][C:2]1[C:3]([OH:13])=[C:4]([O:11][CH3:12])[C:5]([Cl:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:14]OS(OC)(=O)=O>C1COCC1>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([O:11][CH3:12])[C:5]([Cl:10])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 867140745-Bromo-2-chloro-4-hydroxy-3-methoxybenzaldehyde

Product 1

HCID 867140735-Bromo-2-chloro-3,4-dimethoxybenzaldehydeYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To the mixture of aldehyde 156 (15.0 g, 56.5 mmol) in THF (300 mL) were added dimethylsulfate (7.0 mL, 73.5 mmol) and LiOH monohydrate (3.1 g, 73.5 mmol). The mixture was stirred for 3 hours at 65° C. The mixture was cooled to r.t. and filtered to remove insoluble materials through celite. The filtrate was extracted with EtOAc/aq. 50% NaCl solution (200 mL/500 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the compound 157 (11.1 g, 70%).

Workup

  1. temperatureThe mixture was cooled to r.t.
  2. filtrationfiltered
  3. customto remove insoluble materials through celite
  4. extractionThe filtrate was extracted with EtOAc/aq
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cf0610b973134597be3c52ea8dfc61d5
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

Loading…