Methanol → HCID 86627035, compound

HRID 2097480Notes

Reaction equation

HRID 2097480 reaction equation
CO.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]([F:13])[F:12])=[C:6]([O:14][CH:15]([CH:22]2[CH2:24][CH2:23]2)[C:16]#[C:17][Si](C)(C)C)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]([F:13])[F:12])=[C:6]([O:14][CH:15]([CH:22]2[CH2:24][CH2:23]2)[C:16]#[CH:17])[CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 66602650HCID 66602650, compound

Product 1

HCID 86627035HCID 86627035, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 34 ml of methanol solution containing 4.05 g (10.5 mmol) of 4-bromo-2-(1-cyclopropyl-3-trimethylsilyl-2-propynyloxy)-1-difluoromethoxybenzene obtained in Reference example 14-(a) was added 0.48 g (3.5 mmol) of potassium carbonate, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, 50 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=9:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 2.8 g of the title compound as colorless liquid. (Yield: 84%)

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer after separation
  4. washwas washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionthe fractions containing the desired compound
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-94e5dc2bcaa74d97896934f02dc1d87e
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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