Hydrochloric Acid → Methyl 2-Fluoro-5-nitrobenzoate

HRID 80508Notes

Reaction equation

HRID 80508 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH3:15]O>>[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([O:6][CH3:15])=[O:5]

Participants

4

Reactant 3

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

Product 1

HCID 11217860Methyl 2-Fluoro-5-nitrobenzoate

Conditions

Temperature
70 °C

Procedure

To a solution of 2-fluoro-5-nitrobenzoic acid (5 g, 27.0 mmol) in methanol (135 mL) was added HCl (2.66 mL, 32.4 mmol, 12.2M), and the mixture was heated with an oil bath at 70° C. for 24 hours. The solvent was evaporated, and the residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate and brine, dried over sodium sulfate, and concentrated to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.63 (dd, J=3.0, 6.2, 1H), 8.58-8.50 (m, 1H), 7.74-7.61 (m, 1H), 3.92 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ea84a08026924be294c3a9119b20fc08
Source dataset
uspto-grants-2014_09
Patent number
US08846663B2

Reaction notes

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