Dimethylformamide → Methyl 3-fluoro-4-nitrobenzoate

HRID 1796343Notes

Reaction equation

HRID 1796343 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].[CH3:14]N(C=O)C.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:14][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 592761Methyl 3-fluoro-4-nitrobenzoateYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a 500 ml flask under nitrogen atmosphere was charged 3-fluoro-4-nitro benzoic acid (10 g, 0.054 mol, 1 eq) and 250 ml of Toluene followed by DMF (210 ul, 3.7 mmol, 0.05 eq) and was heated to 70° C. At 40° C. thionyl chloride (8.0 ml, 0.11 mol, 2.0 eq) was added and the reaction was allowed to stir at 70° C. for 16 hours. The reaction was removed from the heat and placed in an ambient temperature bath. 100 ml of anhydrous methanol was added and then concentrated on rotary evaporator under reduced pressure, and bath temp of 45° C. The final volume was reduced to ˜70 ml and slowly add hexane 100 ml with stiring to yield a light yellow solid, yield 97%. 1H NMR (Solvent CDCl3), Singlet, 3 H, 3.99 ppm, Doublet of Doublets, 2H, 7.95 ppm, Triplet, 1H, 8.15 ppm. Thin Layer Chromatography elution 5% methanol/dichloromethane, Rf=0.9.

Workup

  1. customThe reaction was removed from the
  2. temperatureheat
  3. customplaced in an ambient temperature
  4. addition100 ml of anhydrous methanol was added
  5. concentrationconcentrated on rotary evaporator under reduced pressure, and bath temp of 45° C
  6. customto yield a light yellow solid, yield 97%
  7. washThin Layer Chromatography elution 5% methanol/dichloromethane, Rf=0.9

Sources & evidence

ORD record
ord-a11d508e318f4dbb80c704dc2adca728
Source dataset
uspto-grants-2006_04
Patent number
US07030150B2

Reaction notes

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