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

HRID 1610160Notes

Reaction equation

HRID 1610160 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-d5f3111cdec445bf823aa8e262abc1b8
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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