Nitric Acid → Methyl 2,6-Difluoro-3-nitrobenzoate

HRID 590222Notes

Reaction equation

HRID 590222 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]>S(=O)(=O)(O)O>[F:5][C:6]1[C:15]([N+:1]([O-:4])=[O:2])=[CH:14][CH:13]=[C:12]([F:16])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 518798Methyl 2,6-difluorobenzoate

Product 1

HCID 43449035Methyl 2,6-Difluoro-3-nitrobenzoateYield 80.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Fuming nitric acid (11 g, 174 mmol) was added to a solution of methyl 2,6-difluorobenzoate (25 g, 145 mmol) in concentrated sulfuric acid (50 mL) at 0° C., and the reaction was stirred for 30 min at 0° C. The reaction mixture was poured over ice-water. The precipitate was filtered off by suction to give the desired product of Step B (25.1 g, 80.6%). 1H NMR (400 MHz, CDCl3) δ ppm 8.13-8.20 (m, 1H), 7.02-7.10 (m, 1H), 3.93 (s, 3H).

Workup

  1. filtrationThe precipitate was filtered off by suction

Sources & evidence

ORD record
ord-1eb4237a28134589a57c4703cda7972c
Source dataset
uspto-grants-2016_01
Patent number
US09233956B2

Reaction notes

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