2-Fluoro-4-nitrophenol → HCID 59424472, compound

HRID 1710923Notes

Reaction equation

HRID 1710923 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([S:11]([N:14]([O:16][CH3:17])[CH3:15])(=[O:13])=[O:12])[S:10][C:3]=12.[F:18][C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[OH:28].C([O-])([O-])=O.[K+].[K+]>C1(OC2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl>[F:18][C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[O:28][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([S:11]([N:14]([O:16][CH3:17])[CH3:15])(=[O:13])=[O:12])[S:10][C:3]=12

Participants

6

Reactant 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 59424482HCID 59424482, compound

Product 1

HCID 59424472HCID 59424472, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7583Diphenyl EtherSolvent

Procedure

A mixture of 82 (400 mg, 1.37 mmol), 2-fluoro-4-nitrophenol (321 mg, 2.05 mmol) and K2CO3 (756 mg, 5.48 mmol) were heated to 190° C. in diphenyl ether (55 ml) for 3 hrs. The mixture was cooled to room temperature, diluted with DCM and filtered. The filtrate was concentrated and purified by column chromatography (eluent EtOAc:hexane, 1:1) to afford title compound 83 (225 mg, 40% yield). MS (m/z) 414.0 (M+H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified by column chromatography (eluent EtOAc:hexane, 1:1)

Sources & evidence

ORD record
ord-099e247d70734ec7bc05e1b45d859035
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

Loading…