Benzyl Bromide → 1-(Benzyloxy)-3-bromo-5-chlorobenzene

HRID 2273973Notes

Reaction equation

HRID 2273973 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:16]([O:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Br:1])[CH:3]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 226301803-Bromo-5-chlorophenol

Product 1

HCID 532170081-(Benzyloxy)-3-bromo-5-chlorobenzeneYield 90%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

2.54 g 3-Bromo-5-chloro-phenol was dissolved in 50 mL acetone. Subsequently were added 8.04 g potassium carbonate, 1.52 mL benzyl bromide and 0.86 g tetrabutylammonium iodide. The mixture was refluxed for 2 h., cooled to room temperature and filtrated, and the filtrate was concentrated to dryness. The residue was chromatographed over a short column of silica, eluting with DCM/PA 1:4, and the pink color of the product fractions (at the front) was removed with active carbon. After filtration and evaporation, 3.11 g (90%) of a pale yellow oil was obtained. 1H NMR (400 MHz, CDCl3) δ 5.03 (s, 2H), 6.92 (t, J=2 Hz, 1H), 7.03 (t, J=2 Hz, 1H), 7.12 (t, J=1.5 Hz, 1H), 7.31-7.45 (m, 5H).

Workup

  1. temperatureThe mixture was refluxed for 2 h.
  2. filtrationfiltrated
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe residue was chromatographed over a short column of silica
  5. washeluting with DCM/PA 1:4
  6. customthe pink color of the product fractions (at the front) was removed with active carbon
  7. filtrationAfter filtration and evaporation

Sources & evidence

ORD record
ord-bf011c4b5ed74a3fb22e58b8999de6c1
Source dataset
uspto-grants-2015_09
Patent number
US09126942B2

Reaction notes

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