Homoallyl bromide → HCID 89872739, compound

HRID 515387Notes

Reaction equation

HRID 515387 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:16][CH2:17][CH:18]=[CH2:19]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:19][CH2:18][CH:17]=[CH2:16])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 21241Homoallyl bromideHCID 24758Sodium hydrideHCID 316783Methyl 2-(4-bromophenyl)acetate

Product 1

HCID 89872739HCID 89872739, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-bromophenylacetate (1 g, 4.37 mmol) in DMF (12 ml) at room temperature was added 60% NaH (0.227 g, 5.68 mmol) and the mixture was stirred at room temperature for 1 hr then was added 4-bromo-1-butene (0.487 ml, 4.80 mmol). The reaction was stirred at room temperature overnight. The reaction was quenched by sat. aq. NH4Cl and was extracted with EtOAc. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (0 to 30% DCM/Hep) to give the title compound 1.1 g (yield 89%). Retention time 1.54 min (condition A).

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. customThe reaction was quenched by sat. aq. NH4Cl
  3. extractionwas extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (0 to 30% DCM/Hep)

Sources & evidence

ORD record
ord-99ca6cba9ba14c65864776e7f69e571e
Source dataset
uspto-grants-2015_08
Patent number
US09108956B2

Reaction notes

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