Pentafluorophenol → HCID 18461402, compound

HRID 2303879Notes

Reaction equation

HRID 2303879 reaction equation
[H-].[Na+].[F:3][C:4]1[C:9]([OH:10])=[C:8]([F:11])[C:7]([F:12])=[C:6]([F:13])[C:5]=1[F:14].Cl[C:16]1[CH:17]=[CH:18][C:19]([N+:31]([O-:33])=[O:32])=[C:20]([N:22](C)[C:23](=O)OC(C)(C)C)[CH:21]=1>CN(C)C=O>[CH3:23][NH:22][C:20]1[CH:21]=[C:16]([O:10][C:9]2[C:4]([F:3])=[C:5]([F:14])[C:6]([F:13])=[C:7]([F:12])[C:8]=2[F:11])[CH:17]=[CH:18][C:19]=1[N+:31]([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 13041PentafluorophenolHCID 24758Sodium hydrideHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 18461402HCID 18461402, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (55 wt. %, 1.66 g) in anhydrous N,N-dimethylformamide (50 ml) was added pentafluorophenol (6.38 g). The mixture was stirred at ambient temperature for several minutes. To this mixture was added t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate (10 g) in small portions and the mixture was stirred at 150° C. for 15 hours. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane/toluene=4/1 as the eluant to give the title compound (2.2 g).

Workup

  1. stirringthe mixture was stirred at 150° C. for 15 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate and water
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-a7537a0c15434371b161e35376bfce2d
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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