Triethylamine → HCID 21938659, compound

HRID 2087035Notes

Reaction equation

HRID 2087035 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C(N(CC)CC)C.[C:19](Cl)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21].[H][H]>C(Cl)Cl.C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([O:11][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 5209483-Fluoro-4-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 21938659HCID 21938659, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 7.0 g (0.045 mol) of 3-fluoro-4-nitrophenol and 6.7 g (0.067 mol) of triethylamine in 20 ml of methylene chloride cooled to 0° is added 6.5 g (0.054 mol) of pivaloyl chloride in a dropwise manner. The reaction is allowed to warm to room temperature and stirred overnight. The reaction is quenched with water and extracted with ethyl acetate. The organic layer is washed successively with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine, and then dried over magnesium sulfate. Filtration and removal of the solvents gives crude 2-fluoro-4-pivaloyloxy-nitrobenzene which is dissolved in 200 ml of absolute ethanol. To the solution is added 0.9 g of 5% palladium on carbon, and the mixture is then hydrogenated under 30 psi hydrogen for two hours. The catalyst is filtered and the solvent removed to give 2-fluoro-4-pivaloyloxyaniline.

Workup

  1. temperaturecooled to 0°
  2. customThe reaction is quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed successively with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration and removal of the solvents
  7. customgives crude 2-fluoro-4-pivaloyloxy-nitrobenzene which
  8. filtrationThe catalyst is filtered
  9. customthe solvent removed

Sources & evidence

ORD record
ord-2e5cbbfc5ed7444c864adef7a2440bcd
Source dataset
uspto-grants-2004_04
Patent number
US06727281B2

Reaction notes

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