Potassium Carbonate → HCID 69937938, compound

HRID 1897582Notes

Reaction equation

HRID 1897582 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].C(=O)([O-])[O-].[K+].[K+].CCN(C(C)C)C(C)C.[CH2:25]([O:27][CH:28]([O:31][CH2:32][CH3:33])[CH2:29]Br)[CH3:26]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:29][CH:28]([O:31][CH2:32][CH3:33])[O:27][CH2:25][CH3:26])=[CH:4][C:3]=1[F:9]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 81531DiisopropylethylamineHCID 27245234-Chloro-3-fluorophenol

Product 1

HCID 69937938HCID 69937938, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 4-chloro-3-fluorophenol (3.66 g, 25 mmol) in DMF (30 ml) at room temperature was added potassium carbonate (6.91 g, 50.0 mmol), DIEA (8.73 ml, 50.0 mmol) and then bromoacetaldehyde diethylacetal (7.52 ml, 50.0 mmol). The mixture was stirred at 100° C. for 16 hr. The mixture was cooled to room temperature and then quenched with water and extracted with EtOAc two times, dried over magnesium sulfate, filtered, concentrated. The residue was purified via Biotage (0-20% AcOEt/heptane; SNAP25 column) giving 13a (6.87 g, quant) as a colorless oil.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with water
  3. extractionextracted with EtOAc two times
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via Biotage (0-20% AcOEt/heptane; SNAP25 column)

Sources & evidence

ORD record
ord-8a38114087424c43918c459d84b33f4b
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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