Diethyl Ether → 4-Bromo-1-{[(2-fluorophenyl)methyl]oxy}-2-(methyloxy)benzene

HRID 1717197Notes

Reaction equation

HRID 1717197 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Br.C(OCC)C>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[F:17])=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 2622344-Bromo-2-methoxyphenol

Product 1

HCID 594689134-Bromo-1-{[(2-fluorophenyl)methyl]oxy}-2-(methyloxy)benzeneYield 95.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-bromo-2-(methyloxy)phenol (3.0 g, 14.78 mmol), potassium carbonate (2.99 g, 22.17 mmol) and 2-fluorobenzylbromide (1.78 ml, 14.78 mmol) in acetonitrile (20 ml) was stirred at room temperature overnight. Diethylether was added. The organic phase was then washed with water and 1M NaOH, dried (Na2SO4), filtered and evaporated to afford the title compound (4.388 g, quant.). Rt (HPLC): 6.25 min; 1H-NMR (400 MHz, DMSO-d6) δ(ppm): 7.5 (m, 1H), 7.4 (m, 1H), 7.2 (m, 2H), 7.1 (s, 1H), 7.0 (m, 2H), 5.1 (s, 2H), 3.7 (s, 3H).

Workup

  1. washThe organic phase was then washed with water and 1M NaOH
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-cd7c2634aef64c3aaa0445a42b61b5e0
Source dataset
uspto-grants-2010_09
Patent number
US07803833B2

Reaction notes

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