Allyl Alcohol → 3-(4-Bromophenyl)propanal

HRID 1916578Notes

Reaction equation

HRID 1916578 reaction equation
C([O-])(O)=O.[Na+].[Br:6][C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=1.[CH2:14]([OH:17])[CH:15]=[CH2:16]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:16][CH2:15][CH:14]=[O:17])=[CH:9][CH:8]=1

Participants

8

Reactant 3

HCID 7858Allyl AlcoholHCID 115221-Bromo-4-iodobenzeneHCID 516892Sodium Bicarbonate

Product 1

HCID 114812883-(4-Bromophenyl)propanal

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

210 mg (0.86 mmol) Pd(OAc)2, 5.23 g (17.32 mmol) tetra-n-butylammonium chloride and 3.6 g NaHCO3 are added to a solution of 5.0 g (17.32 mmol) 4-bromo-iodo-benzene and 3.0 mL (43.67 mmol) allylalcohol in 30 mL DMF. The reaction solution is stirred for 2 h at 60° C. and diluted with 50 mL water. The aqueous phase is extracted with 50 mL EtOAc and the combined organic extracts are washed with 50 mL saturated NaCl solution. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Further purification is carried out by column chromatography on silica gel (cyc/EtOAc 3:1).

Workup

  1. extractionThe aqueous phase is extracted with 50 mL EtOAc
  2. washthe combined organic extracts are washed with 50 mL saturated NaCl solution
  3. dry with materialThe organic phase is dried over Na2SO4
  4. customFurther purification

Sources & evidence

ORD record
ord-e1b1308489f745358b8920534d10b34c
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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