Hydrochloric Acid → HCID 58444564, compound

HRID 1509765Notes

Reaction equation

[Bi](Br)(Br)[Br:2].[Br:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[F:14].[CH2:15]([CH:17]([CH:20]=[CH2:21])[CH2:18]O)[CH3:16].Cl>C1(C)C=CC=CC=1>[Br:2][CH:15]1[CH:17]([CH2:20][CH3:21])[CH2:18][O:11][CH:10]([C:9]2[CH:12]=[CH:13][C:6]([Br:5])=[C:7]([F:14])[CH:8]=2)[CH2:16]1

Participants

Conditions

Temperature: 10 °C

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.

Workup

customthe organic phase is separated off
extractionThe aqueous phase is extracted with toluene
washthe combined organic phases are washed successively with water, saturated sodium hydrogen-carbonate solution and saturated sodium chloride solution
customThe solution is dried
concentrationconcentrated to dryness
customThe crude product is purified by column chromatography (SiO2, n-heptane:toluene=2:1)

Sources & evidence

ORD record: ord-3d5c2e053fc14ce78b8460cad8562c14
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211513B2

Reaction notes

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