Acetic Acid → 2-(2-Fluoro-6-nitrophenyl)ethan-1-ol

HRID 1609094Notes

Reaction equation

HRID 1609094 reaction equation
N([O-])=O.[Na+].S(=O)(=O)(O)O.C(O)(=O)C.N[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([CH2:24][CH2:25][OH:26])[C:16]=1[F:27]>C(Cl)(Cl)Cl.C(O)C>[F:27][C:16]1[C:17]([CH2:24][CH2:25][OH:26])=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][CH:15]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 207922134-Amino-3-fluoro-2-(2-hydroxyethyl)nitrobenzeneHCID 23668193Sodium Nitrite

Product 1

HCID 156914472-(2-Fluoro-6-nitrophenyl)ethan-1-olYield 46.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

While cooling on ice, 6.52 g (94.5 mmol) of sodium nitrite was added to 45 ml of concentrated sulfuric acid through 30 minutes. Then, 180 ml of acetic acid solution containing 14.5 g (72.9 mmol) of the compound (124) obtained in Reference Example 6 was dropped to the solution through 1.5 hours below 20° C. The solution was stirred for 20 minutes. The solution was dropped to 300 ml ethanol suspension containing 40.9 g (285.8 mmol) of cuprous oxide. The reaction solution was heated at 50° C. and was stirred for minutes. The solution was added to 1.0 l of ice/water, and 1.0 l of chloroform was added to the solution. The insoluble matter was filtered off, and the organic layer was separated. After drying over magnesium sulfate, the solvent was removed by distillation, and the residue was separated by column chromatography (silica gel 500 g, eluent solvent; chloroform) to obtain 6.22 g of the subject compound (185) in a 46% yield.

Workup

  1. customobtained in Reference Example 6
  2. additionwas dropped to the solution through 1.5 hours below 20° C
  3. stirringwas stirred for minutes
  4. additionwas added to the solution
  5. filtrationThe insoluble matter was filtered off
  6. customthe organic layer was separated
  7. dry with materialAfter drying over magnesium sulfate
  8. customthe solvent was removed by distillation
  9. customthe residue was separated by column chromatography (silica gel 500 g, eluent solvent; chloroform)

Sources & evidence

ORD record
ord-2bede472cb2448cbbe232b25f8d0b27c
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

Loading…