Acetic Acid → 2-Chloro-4-fluoro-6-nitrophenol

HRID 1189103Notes

Reaction equation

HRID 1189103 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(O)(=O)C.[N+:14]([O-])([OH:16])=[O:15]>O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:14]([O-:16])=[O:15])[C:3]=1[OH:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 748142-Chloro-4-fluorophenol

Product 1

HCID 37278862-Chloro-4-fluoro-6-nitrophenolYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-Chloro-4-fluorophenol (5.64 g, 38.5 mmol) was added to a solution of acetic acid (16.5 mL), nitric acid (8.66 mL) and water (7.5 mL) at 0° C. The reaction mixture was stirred vigorously for 5 hours at 0° C. The resulting precipitate was filtered, washed with water and dried under vacuum to yield 2-chloro-4-fluoro-6-nitrophenol (6.12 g, 32.0 mmol, 83%) as a yellow powder.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-3628c332724f484f81968f0803e927fd
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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