p-Fluoronitrobenzene → HCID 66580037, compound

HRID 2092657Notes

Reaction equation

HRID 2092657 reaction equation
[F:1][C:2]([F:7])([F:6])[CH2:3][CH2:4][OH:5].F[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([O:5][CH2:4][CH2:3][C:2]([F:7])([F:6])[F:1])=[CH:10][CH:11]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 10796Cesium carbonateHCID 1375123,3,3-Trifluoro-1-propanol

Product 1

HCID 66580037HCID 66580037, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of a 3,3,3-trifluoro-propan-1-ol (6.22 g) in acetonitrile (200 ml) kept at RT under an argon atmosphere were added 1-fluoro-4-nitro-benzene (10.1 g) and Cs2CO3 (28.7 g) and the mixture was heated to 100° C. for 18 h. The reaction mixture was cooled to RT and partitioned between AcOEt and ice water. The layers were separated, dried, over Na2SO4 and the solvent was evaporated. The residue was purified by flash chromatography (silica gel; eluent: AcOEt/heptane:gradient 3 to 5%) to afford 1-nitro-4-(3,3,3-trifluoro-propoxy)-benzene as light yellow liquid (3.5 g). MS (EI, m/e): 235.0 (M+).

Workup

  1. customkept at RT under an argon atmosphere
  2. temperatureThe reaction mixture was cooled to RT
  3. custompartitioned between AcOEt and ice water
  4. customThe layers were separated
  5. dry with materialdried, over Na2SO4
  6. customthe solvent was evaporated
  7. customThe residue was purified by flash chromatography (silica gel; eluent: AcOEt/heptane:gradient 3 to 5%)

Sources & evidence

ORD record
ord-c90df496229b43eda94e2a254dda101d
Source dataset
uspto-grants-2013_05
Patent number
US08440710B2

Reaction notes

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