Methanol → 1-Fluoro-2-(methoxymethyl)-4-nitrobenzene

HRID 391736Notes

Reaction equation

HRID 391736 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[F:12].[CH3:13][OH:14]>C1(C)C=CC=CC=1.[Ag-]=O>[F:12][C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[CH2:2][O:14][CH3:13]

Participants

5

Reactant 2

HCID 887MethanolHCID 103539672-(Bromomethyl)-1-fluoro-4-nitrobenzene

Product 1

HCID 594102191-Fluoro-2-(methoxymethyl)-4-nitrobenzene

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

30 g (128 mmol) of the compound from Example 26A are dissolved in 1.3 l of anhydrous toluene, and 45 g (192 mmol) of silver(I) oxide and 24.6 g (769 mmol) of anhydrous methanol are added. The mixture is heated at 60° C. for 16 h. The mixture is then allowed to cool and filtered through silica gel. The product is eluted fractionally using a gradient of cyclohexane and cyclohexane/ethyl acetate 25:1. The product fractions are evaporated to dryness under reduced pressure and dried under reduced pressure. This gives 17 g (72% of theory) of the desired product.

Workup

  1. temperatureto cool
  2. filtrationfiltered through silica gel
  3. washThe product is eluted fractionally
  4. customThe product fractions are evaporated to dryness under reduced pressure
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-25c0478c080a4068bf8b0e69e4a1fd6c
Source dataset
uspto-grants-2013_02
Patent number
US08383822B2

Reaction notes

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