Citric Acid → 2-Fluoro-1,3-dimethoxy-4-nitrobenzene

HRID 2059614Notes

Reaction equation

HRID 2059614 reaction equation
[CH3:1][O-:2].[Na+].[Na].F[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8](F)[C:7]=1[F:16].C(O)(=O)C[C:19](CC(O)=O)(C(O)=O)[OH:20]>CO>[CH3:19][O:20][C:8]1[C:7]([F:16])=[C:6]([O:2][CH3:1])[CH:11]=[CH:10][C:9]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 698711,2,3-Trifluoro-4-nitrobenzeneHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 104654172-Fluoro-1,3-dimethoxy-4-nitrobenzeneYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A freshly prepared solution of sodium methoxide [0.58 g (25 mmol) of sodium dissolved in 3 mL of anhydrous methanol] was added dropwise to a solution of 2 g (11.2 mmol) of 1,2,3-trifluoro-4-nitrobenzene in 30 mL of anhydrous methanol under nitrogen at +4° C. The resulting mixture was stirred overnight at room temperature and quenched with 1 M aqueous citric acid (0.1 eq) and methanol was evaporated under reduced pressure. The residue was taken up with ether, washed with 1 M citric acid, brine and dried over anhydrous magnesium sulfate and filtered off. The filtrate was evaporated under reduced pressure to give 2.2 g (99% yield) of the crude product, which was purified by crystallisation from hexane. H1 NMR (CDCl3) 3.95 (s, 3H, OMe); 4.06 (d, 3H, J=1.6 Hz); 6.72 (dd, 1H, CH, J=9.4 Hz, J=7.5 Hz) 7.72 (dd, 1H, CH, J=9.4 Hz, J=2.23 Hz).

Workup

  1. customwas evaporated under reduced pressure
  2. washwashed with 1 M citric acid, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered off
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-035a0fd2b37d406b8f91b367115713ca
Source dataset
uspto-grants-2012_10
Patent number
US08278290B2

Reaction notes

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