Nitric Acid → 2-(4-Chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-3-chloro-5-trifluoromethylpyridine

HRID 1934311Notes

Reaction equation

HRID 1934311 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[C:11]([OH:12])=[CH:10][C:9]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=2)=[C:8]([F:24])[CH:7]=1>S(=O)(=O)(O)O>[Cl:5][C:6]1[CH:7]=[C:8]([F:24])[C:9]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=2)=[C:10]([N+:1]([O-:4])=[O:2])[C:11]=1[OH:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 118235682-Chloro-5-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-fluorophenol

Product 1

HCID 224661452-(4-Chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-3-chloro-5-trifluoromethylpyridineYield 79%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
20 °C

Procedure

0.24 ml (5.8 mmol) of 100% strength nitric acid was added to 1.9 g (5.8 mmol) of 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-chloro-5-trifluoromethylpyridine in 50 ml of concentrated sulfuric acid. The reaction mixture was stirred at about 20° C. for 10 hours and then poured into 100 ml of ice-water. The solids were subsequently removed and dried at 40° C. in a vacuum drying cabinet. Yield: 79%; m.p.: 67-72° C.

Workup

  1. customThe solids were subsequently removed
  2. customdried at 40° C. in a vacuum
  3. customdrying cabinet

Sources & evidence

ORD record
ord-e1b7ff752b334c3abddc71e5f62eddf9
Source dataset
uspto-grants-2002_05
Patent number
US06383986B1

Reaction notes

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