2-Fluoro-4-nitrophenol → HCID 59424673, compound

HRID 1261225Notes

Reaction equation

HRID 1261225 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]=[CH:13][N:14]([CH2:17][CH3:18])[C:15]=3[CH3:16])[S:10][C:3]=12.C(=O)([O-])[O-].[K+].[K+].[F:25][C:26]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:27]=1[OH:35]>C1(OC2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl>[CH2:17]([N:14]1[C:15]([CH3:16])=[C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[O:35][C:27]3[CH:28]=[CH:29][C:30]([N+:32]([O-:34])=[O:33])=[CH:31][C:26]=3[F:25])[CH:8]=2)[N:12]=[CH:13]1)[CH3:18]

Participants

6

Reactant 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 59424433HCID 59424433, compound

Product 1

HCID 59424673HCID 59424673, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7583Diphenyl EtherSolvent

Procedure

A suspension of 87 (650 mg, 2.35 mmol), potassium carbonate (970 mg, 7.04 mmol) and 2-fluoro-4-nitrophenol (738 mg, 4.7 mmol) were heated at 190° C. in diphenyl ether (15 ml) for 3 hrs. The mixture was cooled to room temperature, diluted with DCM and filtered. The filtrate was concentrated and the residue was purified by column chromatography (eluents EtOAc, then MeOH:EtOAc, 1:9) to afford title compound 88 (600 mg, 64%) as a yellow solid. MS (m/z) 399.0 (M+H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by column chromatography (eluents EtOAc

Sources & evidence

ORD record
ord-601537078d4449779890b5c10edb395f
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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