Cesium fluoride → HCID 22498336, compound

HRID 984503Notes

Reaction equation

HRID 984503 reaction equation
[NH:1]1[CH2:13][CH2:12][CH2:11][CH:3]([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH2:2]1.F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22].[F-].[Cs+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N+:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:1]1[CH2:13][CH2:12][CH2:11][CH:3]([C:4]([O:6][C:7]([CH3:9])([CH3:10])[CH3:8])=[O:5])[CH2:2]1)([O-:23])=[O:22]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 738951-Fluoro-2-nitrobenzeneHCID 4227171301180-05-2

Product 1

HCID 22498336HCID 22498336, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 437C (10.4 g, 56.1 mmol) in toluene (112 mL) was added 2-fluoronitrobenzene (6.0 mL, 56 mmol) and CsF (852 mg, 5.6. mmol). The reaction mixture was stirred under reflux conditions for 18 h, and allowed to cool to ambient temperature. The mixture was diluted with ethyl acetate (100 mL), washed with 10% HCl (2×50 mL), followed by brine (3×100 mL), then dried (Na2SO4) and evaporated in vacuo to obtain the title compound (16.5 g, 94%). MS (ESI) m/e 307 (M+H)+.

Workup

  1. washwashed with 10% HCl (2×50 mL)
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-19767238f58047c89c8fdb090d7edeb8
Source dataset
uspto-grants-2005_03
Patent number
US06867203B2

Reaction notes

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