Nitric Acid → 6-Fluoro-3-hydroxy-2-nitrobenzoic acid

HRID 1418539Notes

Reaction equation

HRID 1418539 reaction equation
[F:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([OH:11])=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>C[N+]([O-])=O>[F:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([N+:12]([O-:14])=[O:13])[C:5]([OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 27744802-Fluoro-5-hydroxybenzoic acid

Product 1

HCID 450895826-Fluoro-3-hydroxy-2-nitrobenzoic acidYield 17.1%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6-Fluoro-3-hydroxybenzoic acid (100 mg, 0.64 mmol) was dissolved in CH3NO2 (10 mL) and cooled to 0° C. HNO3 (90%, 31 μL, 0.64 mmol) was added and the reaction was left at 0° C. for 4 h and then at room temperature over night. Evaporation and purification by flash chromatography on SiO2 (Toluene-EtOAc-HOAc) gave the product (22 mg). 1H NMR (CD3OD): δ 7.32 (t, J=9.0 Hz, 1 H), 7.15 (dd, J1 =9.3 Hz, J2 =4.4 Hz, 1 H); 13C NMR: δ 164.97, 153.68 (d, J=247 Hz), 148.78, 122.67, 122.56, 122.45, 122.13.

Workup

  1. waitat room temperature over night
  2. customEvaporation and purification by flash chromatography on SiO2 (Toluene-EtOAc-HOAc)

Sources & evidence

ORD record
ord-0d0509d783d34dec8dc9706751fe96ac
Source dataset
uspto-grants-1999_03
Patent number
US05883129

Reaction notes

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