p-Fluoronitrobenzene → 1-Nitro-4-(2,2,2-trifluoro-1,1-dimethyl-ethoxy)-benzene

HRID 2381177Notes

Reaction equation

HRID 2381177 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[F:11][C:12]([F:18])([F:17])[C:13]([CH3:16])([OH:15])[CH3:14].[H-].[Na+]>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:15][C:13]([CH3:16])([CH3:14])[C:12]([F:18])([F:17])[F:11])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 681821,1,1-Trifluoro-2-methylpropan-2-ol

Product 1

HCID 667876401-Nitro-4-(2,2,2-trifluoro-1,1-dimethyl-ethoxy)-benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-fluoro-4-nitro-benzene (2.82 g) and 1,1,1-trifluoro-2-methyl-propan-2-ol (2.3 ml) in DMF (90 ml) under an argon atmosphere was added under ice cooling NaH (0.914 g, 55% suspension in oil) and the mixture was stirred for 3 h at RT. It was then partitioned between diethyl ether and water, the layers were separated, dried over Na2SO4 and the solvent was evaporated off to give 1-nitro-4-(2,2,2-trifluoro-1,1-dimethyl-ethoxy)-benzene as a brown oil (4.9 g) that was used in the next step without further purification.

Workup

  1. customIt was then partitioned between diethyl ether and water
  2. customthe layers were separated
  3. dry with materialdried over Na2SO4
  4. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-d8b56eb2538e440bb84894fd11c95dc4
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

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