Benzyl Bromide → 2-(Benzyloxy)-1,3-dibromobenzene

HRID 2069873Notes

Reaction equation

HRID 2069873 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[OH:9].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:10]([O:9][C:3]1[C:2]([Br:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Br:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 118472,6-Dibromophenol

Product 1

HCID 145344892-(Benzyloxy)-1,3-dibromobenzeneYield 99.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2,6-Dibromophenol (29.30 g, 116 mmol) and benzyl bromide (33.14 g, 194 mmol) were dissolved in 2-butanone (300 mL). Potassium carbonate (29.47 g, 213 mmol) was added, and the mixture was stirred for 1.5 hr at reflux temperature. The reaction mixture was cooled to room temperature, filtered, and evaporated to dryness. The remaining viscous oil was subjected to silicagel column chromatography, flushing with n-pentane to remove benzyl bromide, then DCM/n-pentane=1:1 to elute the product, yielding the product as a white crystalline solid (39.32 g, 99%). 1H-NMR (CDCl3): δ=7.61 (dd, 2H), 7.54 (d, 2H), 7.41 (m, 3H), 6.90 (t, 1H), 5.04, (s, 2H) ppm.

Workup

  1. temperatureat reflux temperature
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customflushing with n-pentane
  5. customto remove benzyl bromide
  6. washDCM/n-pentane=1:1 to elute the product

Sources & evidence

ORD record
ord-467ddd06c2434f0cbfb6a8b575788b99
Source dataset
uspto-grants-2012_10
Patent number
US08299202B2

Reaction notes

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