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

HRID 1690109Notes

Reaction equation

HRID 1690109 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-6a7e017eae00411a8523a40ae4ba1148
Source dataset
uspto-grants-2012_04
Patent number
US08153623B2

Reaction notes

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