Potassium Carbonate → HCID 57894166, compound

HRID 1822370Notes

Reaction equation

HRID 1822370 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:16]([O:19][CH2:20][CH2:21]Br)(=[O:18])[CH3:17]>CN(C=O)C>[CH2:20]([O:19][C:16](=[O:18])[CH2:17][O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[CH3:9])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 168964-Bromo-2-methylphenol

Product 1

HCID 57894166HCID 57894166, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-bromo-2-methylphenol (10.0 g, 53.5 mmol) and 325 mesh potassium carbonate (11.08 g, 80.2 mmol) in DMF (100 mL) is treated dropwise with bromoethyl acetate (10.71 g, 64.1 mmol) and then stirred for about 20 hours at room temperature under N2. The reaction is filtered, and the filtrate is acidified with 1 N HCl. The mixture is then diluted with water and extracted with Et2O. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 5/1 hexanes/ethyl acetate to afford about 15.01 g (100%) of the titled compound. Rf=0.33 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3).

Workup

  1. filtrationThe reaction is filtered
  2. additionThe mixture is then diluted with water
  3. extractionextracted with Et2O
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. customthe solvent is removed in vacuo
  6. customto afford crude product that
  7. customis absorbed on silica gel
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-ae33e985662246e2ae78e5a3734fb7be
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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