Ethyl bromoacetate → Ethyl 2-(2-acetyl-4-bromophenoxy)acetate

HRID 1403486Notes

Reaction equation

HRID 1403486 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[OH-].[Na+].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C)C=O>[C:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[O:11][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 19261366Ethyl 2-(2-acetyl-4-bromophenoxy)acetateYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(5-bromo-2-hydroxyphenyl)ethan-1-one (10 g, 46.50 mmol) in N,N-dimethylformamide (80 mL) was added sodium hydroxide (2.23 g, 92.92 mmol) and then stirred for 1 hour at room temperature. Ethyl 2-bromoacetate (8.24 g, 49.34 mmol) was added dropwise and stirred overnight at room temperature. The reaction mixture was quenched by the addition of water (200 mL), adjusted to pH 5 with HCl (3N), extracted with ethyl acetate (50 mL×3), dried over anhydrous sodium sulfate, and concentrated under vacuum to give a residue which was purified by silica gel chromatography (5% ethyl acetate in petroleum ether) to afford ethyl 2-(2-acetyl-4-bromophenoxy)acetate as a light yellow oil (8.9 g, 64%).

Workup

  1. stirringstirred overnight at room temperature
  2. customThe reaction mixture was quenched by the addition of water (200 mL)
  3. extractionextracted with ethyl acetate (50 mL×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto give a residue which
  7. customwas purified by silica gel chromatography (5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-6980cfa15c444c7eb6bd621f11a64972
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

Loading…