1,10-Phenanthroline → 3-(2-Bromo-3-methylphenoxy)tetrahydrofuran

HRID 1029044Notes

Reaction equation

HRID 1029044 reaction equation
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:21][C:22]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=1I.[O:30]1[CH2:34][CH2:33][CH:32]([OH:35])[CH2:31]1>[Cu]I.CCOC(C)=O>[Br:21][C:22]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=1[O:35][CH:32]1[CH2:33][CH2:34][O:30][CH2:31]1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 99603-Furanol, tetrahydro-HCID 10796Cesium carbonateHCID 509981582-Bromo-1-iodo-3-methylbenzene

Product 1

HCID 673247303-(2-Bromo-3-methylphenoxy)tetrahydrofuran

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A vial was charged with copper(I) iodide (38.5 mg, 0.202 mmol), 1,10-phenanthroline (72.8 mg, 0.404 mmol), cesium carbonate (1.32 g, 4.04 mmol), 2-bromo-1-iodo-3-methylbenzene (600 mg, 2.021 mmol) and tetrahydrofuran-3-ol (1.80 mL, 22.23 mmol). The vial was sealed and the reaction mixture was heated to 120° C. for 24 h. The reaction mixture was cooled to RT, EtOAc was added and the mixture was filtered through a pad of silica gel. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (25% EtOAc/hexanes). 3-(2-Bromo-3-methylphenoxy)tetrahydrofuran was isolated as a light-yellow oil (178 mg).

Workup

  1. customThe vial was sealed
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationthe mixture was filtered through a pad of silica gel
  4. customThe solvent was removed under reduced pressure
  5. customthe remaining residue was purified by flash chromatography (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a05d2d7c757249b4b787a05d966cacdc
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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