2-Fluoro-4-nitrophenol → HCID 59424608, compound

HRID 500794Notes

Reaction equation

HRID 500794 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[S:29][C:28]4[C:23](=[N:24][CH:25]=[CH:26][C:27]=4Cl)[CH:22]=3)=[CH:17][CH:16]=2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:31][C:32]1[CH:37]=[C:36]([N+:38]([O-:40])=[O:39])[CH:35]=[CH:34][C:33]=1[OH:41].C(=O)([O-])[O-].[K+].[K+].CO.CCOC(C)=O>O(C1C=CC=CC=1)C1C=CC=CC=1.C(Cl)Cl>[Si:1]([O:8][C@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[S:29][C:28]4[C:23](=[N:24][CH:25]=[CH:26][C:27]=4[O:41][C:33]4[CH:34]=[CH:35][C:36]([N+:38]([O-:40])=[O:39])=[CH:37][C:32]=4[F:31])[CH:22]=3)=[CH:17][CH:16]=2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 21584119Ethylacetate methanolHCID 68694568HCID 68694568, compound

Product 1

HCID 59424608HCID 59424608, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7583Diphenyl EtherSolvent

Conditions

Temperature
195 °C

Procedure

To a solution of 100 (250.0 mg, 0.54 mmol) in Ph2O (4 ml) was added 2-fluoro-4-nitrophenol (171 mg, 1.1 mmol) and potassium carbonate (304 mg, 2.2 mmol). The reaction mixture was heated to 195° C. for 3 hrs, cooled to room temperature, diluted with DCM, filtered and concentrated. The residue was purified by column chromatography, eluents EtOAc, then MeOH/EtOAc (20-80), to afford title compound 101 (94 mg, 30% yield) as a white solid. MS (m/z): 580.3 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography, eluents EtOAc

Sources & evidence

ORD record
ord-b54be83a32ec42f1b3dae4a5c4ee2bfb
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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