Methyl Ethyl Ketone → HCID 67059668, compound

HRID 1993140Notes

Reaction equation

HRID 1993140 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8](=O)[CH2:9][CH3:10].[F:12][C:13]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=1[OH:20].BrCC=CC>O>[CH2:7]([O:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([F:19])[C:13]=1[F:12])[CH:8]=[CH:9][CH3:10]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 808792,3-DifluorophenolHCID 1224142-Butene, 1-bromo-

Product 1

HCID 67059668HCID 67059668, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

122 g of anhydrous potassium carbonate was added to a 2-butanone (600 mL) solution containing 77.2 g of 2,3-difluorophenol, and then 90.0 mL of 1-bromo-2-butene (E/Z ratio=92/8) was added thereto. The solution was heated under reflux for 4 hours, then cooled to room temperature, and water was added dropwise thereto to stop the reaction. Extraction was performed with hexane (three times), and the collected organic phase was washed with 3M hydrochloric acid, water, saturated aqueous solution of sodium hydrogencarbonate, and saturated saline in this order, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure (155 to 160° C., 50 kPa), to thereby obtain 106 g of 1-(2-butenoxy)-2,3-difluorobenzene in the form of a colorless and transparent liquid (E/Z ratio=82/18 according to 1H-NM analysis).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 4 hours
  3. customthe reaction
  4. extractionExtraction
  5. washthe collected organic phase was washed with 3M hydrochloric acid, water, saturated aqueous solution of sodium hydrogencarbonate, and saturated saline in this order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure (155 to 160° C., 50 kPa)

Sources & evidence

ORD record
ord-23f31b27cdbf443f85c471f1fb9e9985
Source dataset
uspto-grants-2010_01
Patent number
US07651630B2

Reaction notes

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