1,10-Phenanthroline → HCID 58452045, compound

HRID 1029041Notes

Reaction equation

HRID 1029041 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[CH2:9]([OH:14])[C:10]([CH3:13])([CH3:12])[CH3:11].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]I>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:14][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 13181,10-PhenanthrolineHCID 6404Neopentyl alcoholHCID 10796Cesium carbonateHCID 114151-Bromo-2-iodobenzene

Product 1

HCID 58452045HCID 58452045, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
100 °C

Procedure

A vial was charged with 1-bromo-2-iodobenzene (627 μL, 5 mmol), neopentyl alcohol (4.85 g, 55.0 mmol), copper(I) iodide (95 mg, 0.500 mmol), 1,10-phenanthroline (180 mg, 1.000 mmol) and cesium carbonate (2.28 g, 7.00 mmol). The vial was sealed under air atmosphere and heated to 100° C. for 12 h. The reaction mixture was cooled to RT and filtered through a pad of silica gel. The silica gel was washed with Et2O. The filtrate was concentrated and the residue was purified by column chromatography (100% hexanes) to yield the 1-bromo-2-(neopentyloxy)benzene as a colorless oil.

Workup

  1. customThe vial was sealed under air atmosphere
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through a pad of silica gel
  4. washThe silica gel was washed with Et2O
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by column chromatography (100% hexanes)

Sources & evidence

ORD record
ord-9c70765000ba48edb697a7623c3d6e48
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

Loading…