1,4-Dibromobutane → Ethyl 2-(4-bromobutoxy)acetate

HRID 22964

Reaction equation

HRID 22964 reaction equation
[H-].[Na+].[C:3]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:4][OH:5].[Br:10][CH2:11][CH2:12][CH2:13][CH2:14]Br.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:8]([O:7][C:3](=[O:6])[CH2:4][O:5][CH2:14][CH2:13][CH2:12][CH2:11][Br:10])[CH3:9]

Participants

6

Reactant 4

HCID 80561,4-DibromobutaneHCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate

Product 1

HCID 20436843Ethyl 2-(4-bromobutoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium hydride in 40 mL DMF stirred at 0° C. was slowly added ethyl glycolate (5 g, 48 mmol). After 1 hour, 1,4-dibromobutane (8.6 mL, 72 mmol) was added, and the mixture was stirred for an additional 2 hours. The reaction was allowed to warm to room temperature for an additional 3 hours. A sodium bicarbonate solution was added, and the organic layer was dried over anhydrous sodium sulfate, concentrated and the residue was purified by chromatography to afford a colorless oil.

Workup

  1. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated
  3. customthe residue was purified by chromatography
  4. customto afford a colorless oil

Sources & evidence

ORD record
ord-ab789f9d1df541f2bbe68664d376d405
Source dataset
uspto-grants-2005_02
Patent number
US06849657B2

Linked notes

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