2,4-Difluoronitrobenzene → HCID 117772868, compound

HRID 2281081Notes

Reaction equation

HRID 2281081 reaction equation
[F:1][CH2:2][CH:3]([OH:5])[CH3:4].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.F[C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25]>C1COCC1.O.CCOC(C)=O>[F:23][C:21]1[CH:22]=[CH:17][C:18]([N+:24]([O-:26])=[O:25])=[C:19]([O:5][CH:3]([CH3:4])[CH2:2][F:1])[CH:20]=1

Participants

7

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 1016711-Fluoropropan-2-olHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 117772868HCID 117772868, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

0.29 g (3.77 mmol) 1-fluoro-propan-2-ol in 20 mL THF is cooled down to 0° C. 4.90 mL (1 M in THF; 4.90 mmol) LiHMDS is added drop wise. After 60 minutes of stirring at 0° C. 0.60 g (3.77 mmol) 2,4-difluoro-1-nitro-benzene is added. The mixture is stirred for 2 h. The mixture is diluted with water and EtOAc. The organic layer is washed with brine, separated, dried and evaporated giving rise to the crude 4-fluoro-2-(2-fluoro-1-methyl-ethoxy)-1-nitro-benzene. 80.0 mg palladium on charcoal (10%) and MeOH are added hydrogenated in a Parr apparatus (RT; 50 psi; 5 h). The catalyst is filtered off and the solvent is evaporated.

Workup

  1. stirringThe mixture is stirred for 2 h
  2. washThe organic layer is washed with brine
  3. customseparated
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-07edebd22cb642198036e9ac56b0e46a
Source dataset
uspto-grants-2015_09
Patent number
US09139577B2

Reaction notes

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