Reaction #1596947

Reaction equation

hydrochloric acid

bismuth(III) bromide

4-bromo-3-fluorobenzaldehyde

2-ethylbut-3-en-1-ol

→

4-bromo-2-(4-bromo-3-fluorophenyl)-5-ethyltetrahydropyran

Solvents

toluene

toluene

toluene

Conditions

Workup

1. 1
   Otherthe organic phase is separated off
2. 2
   ExtractionThe aqueous phase is extracted with toluene
3. 3
   Washthe combined organic phases are washed successively with water, saturated sodium hydrogen-carbonate solution and saturated sodium chloride solution
4. 4
   OtherThe solution is dried
5. 5
   Concentrationconcentrated to dryness
6. 6
   OtherThe crude product is purified by column chromatography (SiO2, n-heptane:toluene=2:1)

Procedure

72.9 g (0.16 mol) of bismuth(III) bromide are initially introduced in 50 ml of toluene at −10° C., and a solution of 50.0 g (0.25 mol) of 4-bromo-3-fluorobenzaldehyde in 250 ml of toluene is added dropwise. A solution of 27.0 g (0.27 mol) of 2-ethylbut-3-en-1-ol in 50 ml of toluene is metered in at this temperature, and the mixture is stirred at 10° C. for 2 h. Dilute hydrochloric acid is added to the batch, and the organic phase is separated off. The aqueous phase is extracted with toluene, and the combined organic phases are washed successively with water, saturated sodium hydrogen-carbonate solution and saturated sodium chloride solution. The solution is dried using sodium sulfate and concentrated to dryness. The crude product is purified by column chromatography (SiO2, n-heptane:toluene=2:1), giving 4-bromo-2-(4-bromo-3-fluorophenyl)-5-ethyltetrahydropyran as a colourless oil.

Source