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

HRID 1710922Notes

Reaction equation

HRID 1710922 reaction equation
[C:1]([O:5][C:6](=[O:31])[N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[S:29][C:28]3[C:23](=[N:24][CH:25]=[CH:26][C:27]=3Cl)[CH:22]=2)=[CH:17][CH:16]=1)[CH2:8][CH:9]1[CH2:13][CH2:12][CH2:11][O:10]1)([CH3:4])([CH3:3])[CH3:2].[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:27]1[CH:26]=[CH:25][N:24]=[C:23]2[CH:22]=[C:21]([C:18]3[CH:19]=[CH:20][C:15]([CH2:14][N:7]([CH2:8][CH:9]4[CH2:13][CH2:12][CH2:11][O:10]4)[C:6](=[O:31])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:16][CH:17]=3)[S:29][C:28]=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-1e85a3507e984de3a07c39d923797a28
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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