Methane, dichloromethoxy- → 5-Bromo-2-fluoro-4-methoxybenzaldehyde

HRID 503203Notes

Reaction equation

HRID 503203 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH3:10].[CH3:11][O:12]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([O:9][CH3:10])=[CH:4][C:5]([F:8])=[C:6]([CH:7]=1)[CH:11]=[O:12]

Participants

5

Procedure

8.4 g of 1-bromo-4-fluoro-2-methoxy-benzene obtained in Production Example II-1-a was dissolved in 200 ml of dichloromethane. 21 ml of titanium tetrachloride and 5.6 ml of dichloromethyl methyl ether were added at 0° C. in nitrogen atmosphere, followed by stirring at room temperature for 4.5 hours. Then, the reaction mixture was gradually poured onto ice-water, and extracted with diethyl ether for two times. The organic layer was sequentially washed with each one portion of water, saturated aqueous sodium hydrogencarbonate solution and water, dried over magnesium sulfate and the solvent was evaporated, to give 9.44 g of the title compound as white crystals.

Workup

  1. additionThen, the reaction mixture was gradually poured onto ice-water
  2. extractionextracted with diethyl ether for two times
  3. washThe organic layer was sequentially washed with each one portion of water, saturated aqueous sodium hydrogencarbonate solution and water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1a98b578c18948329aed6fcc6b9c9204
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

Loading…