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

HRID 1883427Notes

Reaction equation

HRID 1883427 reaction equation
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:21]([OH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Br:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1I>[Cu]I.C1(C)C=CC=CC=1>[Br:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:28][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

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

Product 1

HCID 5618281-(Benzyloxy)-2-bromobenzeneYield 71.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A test tube was charged with CuI (20 mg, 0.10 mmol, 0.10 equiv), 1,10-phenanthroline (36 mg, 0.20 mmol, 0.20 equiv), Cs2CO3 (456 mg, 1.4 mmol, 1.4 equiv), benzyl alcohol (207 μL, 2.0 mmol, 2.0 equiv), 2-bromo-iodobenzene (128 μL, 1.0 mmol, 1.0 equiv) and toluene (0.5 mL). The test tube was sealed and the reaction mixture was stirred at 110° C. for 36 h. The resulting suspension was cooled to room temperature and filtered through a 1×1 cm pad of silica gel, eluting with dichloromethane. The filtrate was concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (2×20 cm; pentane:dichloromethane 2:1) provided 187 mg (71% yield) of the title compound as a colorless oil.

Workup

  1. customThe test tube was sealed
  2. temperatureThe resulting suspension was cooled to room temperature
  3. filtrationfiltered through a 1×1 cm pad of silica gel
  4. washeluting with dichloromethane
  5. concentrationThe filtrate was concentrated in vacuo
  6. customPurification of the residue by flash chromatography on silica gel (2×20 cm; pentane:dichloromethane 2:1)

Sources & evidence

ORD record
ord-1a2bec598c3a4c77975cf27f1eaed1af
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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