Nitric Acid → 4-Fluoro-3-nitrophenylacetic acid

HRID 1633607Notes

Reaction equation

HRID 1633607 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 98372-(4-Fluorophenyl)acetic acid

Product 1

HCID 111272614-Fluoro-3-nitrophenylacetic acidYield 70.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 4-fluorophenylacetic acid (10.0 g, 64.9 mmol) in concentrated sulfuric acid (100 ml) was cooled to 0° C. Concentrated nitric acid (4.5 ml, 65 mmol) was added drop-wise, keeping the temperature at 0-5° C. At the end of the addition the mixture was poured into ice-water (400 ml). The precipitate was filtered off, washed thoroughly with water and dried with suction to yield 1i (9.11 g,70%).

Workup

  1. customat 0-5° C
  2. additionAt the end of the addition the mixture
  3. filtrationThe precipitate was filtered off
  4. washwashed thoroughly with water
  5. customdried with suction

Sources & evidence

ORD record
ord-d3b2c81d29b74357838e6d3ae5f1d384
Source dataset
uspto-grants-2003_01
Patent number
US06503925B1

Reaction notes

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