1,2-Difluoro-3-nitrobenzene → Nitrobenzene

HRID 467545Notes

Reaction equation

HRID 467545 reaction equation
F[C:2]1[C:7](F)=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].N1CCC(CNC(=O)OC(C)(C)C)CC1.C(N(CC)C(C)C)(C)C>CCO.CCOC(C)=O>[N+:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1)([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 813351,2-Difluoro-3-nitrobenzeneHCID 81531DiisopropylethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 7416Nitrobenzene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,3-difluoronitrobenzene (5.0 g, 31 mmol) in EtOH (25 mL) were added tert-butyl piperidin-4-ylmethylcarbamate (8.1 g, 38 mmol), and N,N-diisopropylethylamine (6.6 mL, 38 mmol). The reaction was irradiated to 110° C. for 20 min by microwave. The crude reaction mixture was diluted with EtOAc, washed with 1 N HCl and brine, dried over MgSO4 and concentrated to yield nitrobenzene Int-2a (11.2 g, 99%) as yellow crystals. The crude product was used without further purification.

Workup

  1. customThe reaction was irradiated to 110° C. for 20 min by microwave
  2. customThe crude reaction mixture
  3. washwashed with 1 N HCl and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a7276f9a675a4ac396313baed90f7c1a
Source dataset
uspto-grants-2014_01
Patent number
US08623857B2

Reaction notes

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