Water → 4-Bromo-1-[(3-methylbut-3-en-1-yl)oxy]-2-(propan-2-yl)benzene

HRID 402782

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:9]([CH3:11])[CH3:10])[CH:3]=1.Br[CH2:13][CH2:14][C:15]([CH3:17])=[CH2:16].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][CH2:14][C:15]([CH3:17])=[CH2:16])=[C:4]([CH:9]([CH3:11])[CH3:10])[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

4-Bromo-2-isopropylphenol (897 mg, 4.17 mmol) was dissolved in DMF (4.17 mL) and 4-bromo-2-methylbut-1-ene (1.24 g, 8.34 mmol) was added followed by K2CO3 (1.15 g, 8.34 mmol). The reaction mixture was heated to 60° C. overnight, cooled to room temperature, and diluted with Hexanes:EtOAc (1:1). Water was added and the organic layer was separated, dried over Na2SO4, filtered, and concentrated under vacuum. The crude residue was purified by silica gel chromatography, eluting with 0-15% EtOAc/Hexanes to give the title compound as a colorless oil.

Workup

temperaturecooled to room temperature
customthe organic layer was separated
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum
customThe crude residue was purified by silica gel chromatography
washeluting with 0-15% EtOAc/Hexanes

Sources & evidence

ORD record: ord-b499425db2e342b09c0e0d781b637b37
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742110B2

Linked notes

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