1,10-Phenanthroline → 2-Bromo-1-methyl-3-(neopentyloxy)benzene

HRID 1029042Notes

Reaction equation

HRID 1029042 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1I.[CH2:10]([OH:15])[C:11]([CH3:14])([CH3:13])[CH3:12].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]I.C(OCC)C>[Br:1][C:2]1[C:3]([O:15][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 6404Neopentyl alcoholHCID 10796Cesium carbonateHCID 509981582-Bromo-1-iodo-3-methylbenzene

Product 1

HCID 673257132-Bromo-1-methyl-3-(neopentyloxy)benzene

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

A vial was charged with 2-bromo-1-iodo-3-methylbenzene (677 mg, 2.28 mmol), neopentyl alcohol (2.21 g, 25.08 mmol), copper(I) iodide (43.4 mg, 0.228 mmol), 1,10-phenanthroline (82 mg, 0.456 mmol) and cesium carbonate (1.04 mg, 3.19 mmol). The vial was sealed under air atmosphere and heated to 110° C. for 24 h. The reaction mixture was cooled to rt and diethyl ether was added. The suspension was filtered through a pad of silica gel. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (100% hexanes). 2-Bromo-1-methyl-3-(neopentyloxy)benzene was obtained as a colorless oil.

Workup

  1. customThe vial was sealed under air atmosphere
  2. temperatureThe reaction mixture was cooled to rt
  3. filtrationThe suspension 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 (100% hexanes)

Sources & evidence

ORD record
ord-9b910a8d104a44dda92de3b12f1c731f
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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