2-Fluoro-4-nitrophenol → HCID 59424530, compound

HRID 418745Notes

Reaction equation

HRID 418745 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)[S:10][C:3]=12.[F:19][C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=1[OH:29].C(=O)([O-])[O-].[K+].[K+]>C1(OC2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl>[F:19][C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=1[O:29][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)[S:10][C:3]=12

Participants

6

Reactant 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 58790345HCID 58790345, compound

Product 1

HCID 59424530HCID 59424530, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7583Diphenyl EtherSolvent

Conditions

Temperature
170 °C

Procedure

A suspension of 418 (0.638 g, 2.31 mmol), 2-fluoro-4-nitrophenol (0.725 g, 4.61 mmol) and potassium carbonate (0.638 g, 4.61 mmol) in diphenyl ether (6 mL) was heated to 170° C. for 8 h in a pressure tube. The resulting dark solution was cooled to room temperature, diluted with CH2Cl2 and then filtered. The filtrate was concentrated and the residue was purified by flash chromatography (eluent 100% hexanes to 50/50 ethyl acetate/hexanes) to produce title compound 419 as a yellow solid (0.395 g, 43% yield). MS (m/z): 398.0 (M+H).

Workup

  1. temperatureThe resulting dark solution was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by flash chromatography (eluent 100% hexanes to 50/50 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-39761e415a624101bd02b19b20292a13
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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