Phenethyl bromide → HCID 85580920, compound

HRID 1087806Notes

Reaction equation

HRID 1087806 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:6].Br[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C:5]([O:4][CH3:3])=[O:6])=[C:9]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 104196Methyl 4-chlorophenylacetate

Product 1

HCID 85580920HCID 85580920, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 4.35 g of 60% sodium hydride in 50 ml of DMF was added dropwise 20.0 g of methyl 4-chlorophenyl acetate in 25 ml of DMF. Once the evolution had ceased a mixture of 20.0 g of 2-bromoethyl benzene in 25 m of DMF was added and the reaction was stirred at room temPerature overnight. The reaction was then partitioned between 400 ml of ether and 200 ml of H2O. The ether extracts were washed with H2O, dried over magnesium sulfate, filtered and concentrated to 32.9 g of a yellow oil. Chromatography on silica gel with 5% ethyl acetate in hexane afforded 12.6 g of the title compound as a clear, colorless oil.

Workup

  1. additionwas added
  2. customThe reaction was then partitioned between 400 ml of ether and 200 ml of H2O
  3. washThe ether extracts were washed with H2O
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to 32.9 g of a yellow oil

Sources & evidence

ORD record
ord-0f27fc056a2e460c85a1a20b2f571e1e
Source dataset
uspto-grants-1990_10
Patent number
US04960784

Reaction notes

Loading…