Sodium Hydroxide → 4(Fluoromethyl-ethyl)-nitrobenzene

HRID 1379972Notes

Reaction equation

HRID 1379972 reaction equation
[F:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[CH2:4].NOS(O)(=O)=O.S(O)(O)(=O)=O.NO.[OH-].[Na+]>CO>[F:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)[CH3:4]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 159255Hydroxylamine, sulfate (1:1)HCID 13187365HCID 13187365, compound

Product 1

HCID 131873674(Fluoromethyl-ethyl)-nitrobenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 17.5 g (0.1 Mol) 4(1-fluoromethylethenyl)-nitrobenzene in 400 ml CH3OH are added 100 g (0.8 Mol) 90% hydroxylamine-O-sulphonic acid and 67.2 g (0.41 Mol) hydroxylamine sulphate. The reaction mixture is then rendered alkaline (pH 8) at 15°-20° cooling with ice water) with 20% aqueous NaOH. After the addition of a further 500 ml portion of CH3OH the reaction mixture is stirred at room temperature for 24 hours, and then filtered. The filtrate is evaporated in vacuo. The residue is dissolved in CH2Cl2, this solution washed with H2O, dried over Na2SO4 and evaporated. The light yellow, chromatographically (this layer) pure liquid (Rf=0.5; CHCl3 /CCl4 1:1 on silica gel) is vaccum distilled, to give the title compound, b.p. 103°-104°/0.1 Torr.

Workup

  1. customat 15°-20°
  2. filtrationfiltered
  3. customThe filtrate is evaporated in vacuo
  4. dissolutionThe residue is dissolved in CH2Cl2
  5. washthis solution washed with H2O
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-a5bdf1b79488423f819e11151df83b62
Source dataset
uspto-grants-1986_04
Patent number
US04579585

Reaction notes

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