Water → HCID 16641127, compound

HRID 2219191Notes

Reaction equation

HRID 2219191 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14].Br[CH2:16][C:17]([O:19][CH3:20])=[O:18].O>CN(C=O)C.CCOC(C)=O>[CH3:20][O:19][C:17](=[O:18])[CH2:16][O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[Br:7]

Participants

7

Reactant 4

HCID 962WaterHCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 16641127HCID 16641127, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Powdered potassium carbonate (3.84 g, 27.8 mmol) is added to a stirred solution of 2-bromophenol (3.20 g, 18.5 mmol) and methyl bromoacetate (3.11 g, 20.3 mmol) in anhydrous DMF (20 mL). The resultant mixture is stirred at ambient temperature under nitrogen for 16 hours. Water (140 mL) and EtOAc (120 mL) are added to the mixture and the two-layered solution is stirred vigorously for 3 minutes. The organic layer is separated, dried over MgSO4, filtered and concentrated. The crude product is chromatographed oh silica (gradient 2-8% EtOAc in hexane) to give 4.39 g (17.9 mmol, 97% yield) of the title compound. EIMS: m/z 244 (M+, 79Br), 246 (M+, 81Br).

Workup

  1. customThe organic layer is separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is chromatographed oh silica (gradient 2-8% EtOAc in hexane)

Sources & evidence

ORD record
ord-eeed5c0621db49b69d58d031465924b8
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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