Allyl Alcohol → 3-(4-Bromo-2-methylphenyl)propanal

HRID 734834Notes

Reaction equation

HRID 734834 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([CH3:9])[CH:3]=1.[CH2:10]([OH:13])[CH:11]=[CH2:12].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:12][CH2:11][CH:10]=[O:13])=[C:4]([CH3:9])[CH:3]=1

Participants

8

Reactant 3

HCID 7858Allyl AlcoholHCID 516892Sodium BicarbonateHCID 27246015-Bromo-2-iodotoluene

Product 1

HCID 822879023-(4-Bromo-2-methylphenyl)propanal

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 1.00 g (3.39 mmol) of 4-bromo-1-iodo-2-methylbenzene, 0.58 g (10.00 mmol) of allyl alcohol, 0.69 g (8.20 mmol) of sodium bicarbonate, 0.92 g (3.30 mmol) of tetrabutylammonium chloride, and 22 mg (0.10 mmol) of palladium (II) acetate in 5 mL of DMF were stirred for 16 hours at 45° C. under argon. The reaction mixture was diluted with EtOAc, and the organic phase was washed with water, dried over magnesium sulfate, and evaporated down in vacuo. The residue was purified by column chromatography (silica gel, PE/EtOAc 4:1). Yield: 0.60 (78% of theoretical); C10H11BrO (M=227.098); calc.: molpeak (M+H)+: 226/228 (Br); found: molpeak (M+H)+: 226/228 (Br); Rf value: 0.45 (silica gel, PE/EtOAc 4:1).

Workup

  1. washthe organic phase was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated down in vacuo
  4. customThe residue was purified by column chromatography (silica gel, PE/EtOAc 4:1)

Sources & evidence

ORD record
ord-40fa67226683452dbd5c8ffd0ab090eb
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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