4-Bromophenol → 4-(4-Bromophenoxy)tetrahydro-2H-pyran

HRID 1978624Notes

Reaction equation

HRID 1978624 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[O:9]1[CH2:14][CH2:13][CH:12](O)[CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:12]2[CH2:13][CH2:14][O:9][CH2:10][CH2:11]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 162161274-(4-Bromophenoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromophenol (15.0 g), tetrahydropyran-4-ol (9.Og) and triphenylphosphine (23.08 g) in THF (100 ml) was added dropwise at 0° C. diethyl azodicarboxylate (40% toluene solution) (38.3 g), and the mixture was stirred at room temperature for 3 days and concentrated under reduced pressure. To the residue was added diethylether, and precipitated crystals were removed by filtration. The filtrate was concentrated, and the residue was dissolved in ethyl acetate. The solution was washed with 1N sodium hydroxide solution (×3) and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate/hexane=1:4) to give colorless crystals of 4-(4-bromophenyloxy)tetrahydropyran (15.94 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added diethylether
  3. customprecipitated crystals
  4. customwere removed by filtration
  5. concentrationThe filtrate was concentrated
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washThe solution was washed with 1N sodium hydroxide solution (×3) and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified with silica gel column chromatography (ethyl acetate/hexane=1:4)

Sources & evidence

ORD record
ord-391fc2abc7d7478ba9f772af53b9c1ac
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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