Reaction #2139949

Reaction equation

water

ethyldiisopropylamine

6-bromo-3-butoxy-2-fluorophenol

2-methoxyethoxymethyl chloride

→

1-bromo-4-butoxy-3-fluoro-2-(2-methoxyethoxymethoxy)benzene

Yield 99.8%

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.WAITthe mixture was left
2. 2
   Extractionextracted with dichloromethane
3. 3
   Otherevaporated
4. 4
   Filtrationthe crude product was filtered through silica gel with n-heptane/MTB ether (3:1)

Procedure

60.4 ml (0.355 mol) of ethyldiisopropylamine were added with ice-cooling to 77.4 g (0.294 mol) of 6-bromo-3-butoxy-2-fluorophenol dissolved in 500 ml of dichloromethane, 40.3 ml (0.355 mol) of 2-methoxyethoxymethyl chloride were added dropwise, and the mixture was left to stirr overnight at room temperature. The batch was hydrolysed using water, extracted with dichloromethane and evaporated, and the crude product was filtered through silica gel with n-heptane/MTB ether (3:1), giving 103 g (99%) of 1-bromo-4-butoxy-3-fluoro-2-(2-methoxyethoxymethoxy)benzene as a yellow oil.

Source