Dichloromethane → 1-Bromo-3-(1-[4-{2-fluoro-ethoxy}phenyl]-vinyl)-benzene

HRID 1668726Notes

Reaction equation

HRID 1668726 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[F:7][CH2:8][CH2:9]I.[Br:11][C:12]1[CH:13]=[C:14]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH2:19])[CH:15]=[CH:16][CH:17]=1.ClCCl>CN(C)C=O.C1CCCCC1.C(OCC)(=O)C.O>[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:9][CH2:8][F:7])=[CH:24][CH:25]=2)=[CH2:19])[CH:13]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 578252064-[1-(3-Bromo-phenyl)-vinyl]-phenol

Product 1

HCID 578251371-Bromo-3-(1-[4-{2-fluoro-ethoxy}phenyl]-vinyl)-benzeneYield 54.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21867204Cyclohexane ethylacetateSolvent

Conditions

Temperature
55 °C

Procedure

Cesium carbonate (2.18 g, 6.67 mmol, 1.2 eq) and 1-fluoro-2-iodoethane (1.1 g, 6.4 mmol, 1.2 eq) were added to a solution of 4-[1-(3-bromo-phenyl)-vinyl]-phenol (1.5 g, 5.3 mmol, 1.0 eq) in dry N,N-dimethylformamide (15 mL). The mixture was stirred overnight at 55° C.; dichloromethane (100 mL) and water (50 mL) were then added. The organic phase was washed with water (3×) and dried over sodium sulfate. Evaporation of solvent gave crude ether that was purified by flash chromatography (eluent: cyclohexane/ethyl acetate=9:1 then) to give 931 mg (yield 54%) of desired product as yellow oil.

Workup

  1. washThe organic phase was washed with water (3×)
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of solvent
  4. customgave crude ether that
  5. customwas purified by flash chromatography (eluent

Sources & evidence

ORD record
ord-6f4b0b3587484925bb13ad8721ca55a6
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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