Water → 2-(3-bromo-4-fluorophenoxy)tetrahydro-2H-pyran

HRID 1049546Notes

Reaction equation

HRID 1049546 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[O:9][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 27833813-Bromo-4-Fluorophenol

Product 1

HCID 1177599412-(3-bromo-4-fluorophenoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, to a solution of 3-bromo-4-fluorophenol (1.2 g) in toluene (62.8 mL) were added 3,4-dihydro-2H-pyran (1.15 mL) and pyridinium p-toluenesulfonate (0.237 g) at room temperature, and the mixture was stirred for 2 hr. The reaction mixture was poured into water at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (1.63 g) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6df8432126e04cd7ac97d33208fe85eb
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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