2-Fluoro-4-nitrophenol → HCID 59424549, compound

HRID 1261221Notes

Reaction equation

HRID 1261221 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]([CH2:26][CH:27]4[CH2:31][CH2:30][CH2:29][O:28]4)[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:13][CH:12]=3)[S:10][C:3]=12.[F:32][C:33]1[CH:38]=[C:37]([N+:39]([O-:41])=[O:40])[CH:36]=[CH:35][C:34]=1[OH:42].C(=O)([O-])[O-].[K+].[K+]>O(C1C=CC=CC=1)C1C=CC=CC=1.C(Cl)Cl>[F:32][C:33]1[CH:38]=[C:37]([N+:39]([O-:41])=[O:40])[CH:36]=[CH:35][C:34]=1[O:42][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]([CH2:26][CH:27]4[CH2:31][CH2:30][CH2:29][O:28]4)[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:13][CH:12]=3)[S:10][C:3]=12

Participants

6

Reactant 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 59424516HCID 59424516, compound

Product 1

HCID 59424549HCID 59424549, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7583Diphenyl EtherSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of 77 (1.0 g, 2.18 mmol) in Ph2O (10 ml) was added 2-fluoro-4-nitrophenol (856 mg, 5.45 mmol) and potassium carbonate (904 mg, 6.55 mmol). The reaction mixture was heated at 180° C. for 4 hrs, cooled to room temperature, diluted with DCM, filtered and concentrated. The residue was purified by column chromatography, eluent EtOAc:hexane 8:2, to afford title compound 78 (250 mg, 20% yield). 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, eluent EtOAc:hexane 8:2

Sources & evidence

ORD record
ord-1d2b650339134f56bc553cd33fbdab34
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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