Sodium hydride → Methyl 2-(2-acetyl-5-bromophenoxy)acetate

HRID 1930275Notes

Reaction equation

HRID 1930275 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[CH:3]=1.[H-].[Na+].Br[CH2:15][C:16]([O:18][CH3:19])=[O:17]>CN(C=O)C.C(OCC)(=O)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[O:11][CH2:15][C:16]([O:18][CH3:19])=[O:17])(=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 107274031-(4-Bromo-2-hydroxyphenyl)ethan-1-one

Product 1

HCID 57419482Methyl 2-(2-acetyl-5-bromophenoxy)acetateYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(4-bromo-2-hydroxyphenyl)ethanone (1.35 g, 6.28 mmol) in anhydrous DMF (16 mL) was treated in several portions with sodium hydride (377 mg of 60% in oil, 226 mg, 9.42 mmol) followed by stirring at room temperature for 30 min. The mixture was then treated with methyl bromo-acetate (871 μL, 1.45 g, 9.48 mmol) dropwise (solution became warm after addition was complete) followed by stirring at room temperature for 18 h. The mixture was diluted with ethyl acetate and extracted with water (4×) and saturated sodium chloride solution. Drying (Na2SO4) and concentration in vacuo afforded a nearly colorless solid, which was purified by column chromatography on silica gel, eluting with 20-100% ethyl acetate in hexanes. These procedures afforded the title compound as a colorless solid (1.47 g, 82%).

Workup

  1. stirringby stirring at room temperature for 18 h
  2. extractionextracted with water (4×) and saturated sodium chloride solution
  3. customDrying
  4. concentration(Na2SO4) and concentration in vacuo
  5. customafforded a nearly colorless solid, which
  6. customwas purified by column chromatography on silica gel
  7. washeluting with 20-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e63e074f86f846c2bc7a7b747e1838ff
Source dataset
uspto-grants-2012_05
Patent number
US08188104B2

Reaction notes

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