2-Bromopropane → HCID 67323888, compound

HRID 1616937Notes

Reaction equation

HRID 1616937 reaction equation
[Br:1][C:2]1[C:3]([F:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:17]([CH3:19])[CH3:18]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH:17]([CH3:19])[CH3:18])[C:3]=1[F:9]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 184012573-Bromo-2-fluorophenol

Product 1

HCID 67323888HCID 67323888, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 3-bromo-2-fluoro-phenol (2 g, 10 mmol) and cesium carbonate (10 g, 40 mmol) in acetonitrile (20 mL) was added 2-bromopropane (4 mL, 50 mmol). The reaction mixture was stirred at 80° C. for 4 h. The mixture was filtered through a plug of Celite and eluted with ethyl acetate. The resulting solution was evaporated. The residue was purified by flash chromatography on silica gel and eluting with hexanes:EtOAc (1:1) to afford the title product (1.7 g).

Workup

  1. filtrationThe mixture was filtered through a plug of Celite
  2. washeluted with ethyl acetate
  3. customThe resulting solution was evaporated
  4. customThe residue was purified by flash chromatography on silica gel
  5. washeluting with hexanes:EtOAc (1:1)

Sources & evidence

ORD record
ord-3b4c517765b944678391a94b6620727b
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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