Hydrochloric Acid → 2-Fluoro-5-methoxy-4-nitrobenzoic acid

HRID 2234359Notes

Reaction equation

HRID 2234359 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8](F)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:15](=O)([O-])[O-:16].[Cs+].[Cs+].CO.Cl>CN(C=O)C.C(OCC)(=O)C.O>[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:16][CH3:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10796Cesium carbonateHCID 2463752,5-Difluoro-4-nitrobenzoic acid

Product 1

HCID 579556142-Fluoro-5-methoxy-4-nitrobenzoic acidYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,5-Difluoro-4-nitrobenzoic acid (Fluorochem; 100 mg, 0.43 mmol) and caesium carbonate (708 mg, 2.17 mmol) were taken up in dry DMF (2 mL) and dry methanol (120 uL, 2.88 mmol) was added and the reaction stirred at room temperature for 2 hrs. The reaction mixture was diluted with Ethyl Acetate (50 mL) and water (50 mL) and acidified to pH1 with 2N HCl solution. The organics were removed and the aqueous further extracted with Ethyl Acetate (2×50 mL). The combined organics were washed with water (50 mL), brine (50 mL), dried over MgSO4 and concentrated under reduced pressure to give the title compound as a yellow solid (91 mg, 0.42 mmol, 98%).

Workup

  1. customThe organics were removed
  2. extractionthe aqueous further extracted with Ethyl Acetate (2×50 mL)
  3. washThe combined organics were washed with water (50 mL), brine (50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5d13227b8d04ae3a583d59b0fe7a8ec
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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