Dimethylformamide → HCID 20827035, compound

HRID 1785210Notes

Reaction equation

HRID 1785210 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[H-].[Na+].CN(C)C=O.[CH3:17][O:18][C:19](=[O:22])[CH2:20]Br>O>[CH3:17][O:18][C:19](=[O:22])[CH2:20][O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[CH3:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 168964-Bromo-2-methylphenolHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Product 1

HCID 20827035HCID 20827035, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-bromo-2-methylphenol (1.0 g, 5.35 mmol), sodium hydride (0.26 g, 6.42 mmol, 60% mineral oil), N,N-dimethylformamide (10 mL), and methyl-2-bromoacetate (0.56 mL, 5.88 mmol) is stirred at room temperature 18 hr. The mixture is diluted with water (50 mL) and the product extracted to ethyl acetate (3×50 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered, concentrated and purified via silica chromatography eluting with 8:2 hexanes:ethyl acetate to afford title compound as a colorless oil, 1.03 g, 74%. MS M+ 259. The structure is confirmed by 1H NMR spectroscopy.

Workup

  1. extractionthe product extracted to ethyl acetate (3×50 mL)
  2. dry with materialThe combined extracts are dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified via silica chromatography
  6. washeluting with 8:2 hexanes

Sources & evidence

ORD record
ord-96cb7506b94b438cbadc12c2572422eb
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Reaction notes

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