Trimethyl orthoformate → 4-Dimethoxymethyl-2-fluoro-1-nitrobenzene

HRID 1667684Notes

Reaction equation

HRID 1667684 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])C=O.[CH3:13][O:14][CH:15](OC)[O:16][CH3:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO>[CH3:13][O:14][CH:15]([O:16][CH3:17])[C:4]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 38081203-Fluoro-4-nitrobenzaldehyde

Product 1

HCID 540322924-Dimethoxymethyl-2-fluoro-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.5 g (2.96 mmole) of 3-fluoro-4-nitrobenzaldehyde, 1 mL of trimethylorthoformate, 0.020 g of p-toluenesulfonic acid monohydrate and 2 mL of methanol was heated at reflux for 1 hour. The mixture was cooled, and 1 mL of saturated aqueous sodium bicarbonate solution was added. The mixture was concentrated under reduced pressure, and the residue was partitioned between 30 mL of ethyl acetate and 30 mL of saturated aqueous sodium bicarbonate solution. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.64 g of 4-dimethoxymethyl-2-fluoro-1-nitro-benzene (IV.2a) as a pale yellow oil. This material was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperatureThe mixture was cooled
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe residue was partitioned between 30 mL of ethyl acetate and 30 mL of saturated aqueous sodium bicarbonate solution
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-911fb1f5ad1544f5adef44eb3f37e6ad
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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