Hydrochloric Acid → Methyl 2-Fluoro-5-nitrobenzoate

HRID 643552Notes

Reaction equation

HRID 643552 reaction equation
S(Cl)(Cl)=O.Cl.[F:6][C:7]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:19]O>>[F:6][C:7]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=1[C:9]([O:11][CH3:19])=[O:10]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 24386Thionyl ChlorideHCID 2809972-Fluoro-5-nitrobenzoic acid

Product 1

HCID 11217860Methyl 2-Fluoro-5-nitrobenzoate

Procedure

Thionyl chloride (16 mL, 0.22 mol) was added dropwise to cooled (0° C.) methanol (250 mL). After the addition the resulting anhydrous methanolic HCl solution was poured into a flask containing 2-fluoro-5-nitrobenzoic acid (13.77 g, 74.39 mmol). The mixture so obtained was stirred overnight at rt. The reaction mixture was concentrated and the residue collected was purified by flash chromatography using a gradient [silica, 5-30% (700 mL), then 30-50% (1 L)], giving methyl 2-fluoro-5-nitrobenzoate.

Workup

  1. additionwas poured into a flask
  2. customThe mixture so obtained
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue collected
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-5feba9e1ab3a43318421e8a9ac17d8b0
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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