Benzyl Alcohol → 1-(Benzyloxy)-2-bromobenzene

HRID 1029043Notes

Reaction equation

HRID 1029043 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[C:9]1([CH2:15][OH:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]I.C(OCC)C.C1(C)C=CC=CC=1>[CH2:15]([O:16][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 114151-Bromo-2-iodobenzene

Product 1

HCID 5618281-(Benzyloxy)-2-bromobenzene

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

A vial was charged with 1-bromo-2-iodobenzene (0.642 mL, 5 mmol), phenylmethanol (1.036 mL, 10.00 mmol), copper(I) iodide (95 mg, 0.500 mmol), 1,10-phenanthroline (180 mg, 1.000 mmol), cesium carbonate (2281 mg, 7.00 mmol) and toluene (2.5 mL). The vial was sealed under air atmosphere and heated to 110° C. for 36 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 (13% EtOAc/hexanes). 1-(Benzyloxy)-2-bromobenzene was obtained as a yellow 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 (13% EtOAc/hexanes)

Sources & evidence

ORD record
ord-843b3a8e61594a37a398cb6891010f86
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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