Ethyl 4-pentenoate → Ethyl 2-(4-bromo-2-chlorobenzyl)pent-4-enoate

HRID 1013803Notes

Reaction equation

HRID 1013803 reaction equation
[Li+].CC([N-]C(C)C)C.[C:9]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:10][CH2:11][CH:12]=[CH2:13].[Br:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[C:21]([Cl:27])[CH:20]=1>C1COCC1>[Br:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][CH:10]([CH2:11][CH:12]=[CH2:13])[C:9]([O:15][CH2:16][CH3:17])=[O:14])=[C:21]([Cl:27])[CH:20]=1

Participants

5

Reactant 3

HCID 74786Ethyl 4-pentenoateHCID 2724682Lithium diisopropylamideHCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzene

Product 1

HCID 67316264Ethyl 2-(4-bromo-2-chlorobenzyl)pent-4-enoateYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add LDA (5.27 mL, 10.5 mmol, 2.0 M) into a solution of ethyl pent-4-enoate (0.9 g, 7.0 mmol), in THF (125 mL) at −78° C. and stir for 15 minutes. Add 4-bromo-2-chlorobenzyl bromide (3.3 g, 10.5 mmol) and warm reaction to room temperature. Quench with ammonium chloride solution, extract the reaction mixture with methylene chloride and wash the organic layer with brine. Dry over sodium sulfate, filter and concentrate. Purify the residue with silica gel column (hexanes) to afford the title compound (1.65 g, 73%) as colorless oil.

Workup

  1. customreaction to room temperature
  2. customQuench with ammonium chloride solution
  3. extractionextract the reaction mixture with methylene chloride
  4. washwash the organic layer with brine
  5. dry with materialDry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the residue with silica gel column (hexanes)

Sources & evidence

ORD record
ord-6dfe0b384dc14b6a95b76a9869f2ff5d
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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