Isopropanol → HCID 45480464, compound

HRID 386765Notes

Reaction equation

HRID 386765 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9](F)[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:21][CH:22]([OH:24])[CH3:23]>>[Cl:1][C:2]1[CH:10]=[C:9]([O:24][CH:22]([CH3:23])[CH3:21])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 10796Cesium carbonateHCID 72108282-Chloro-4-fluoro-5-nitrobenzoic Acid

Product 1

HCID 45480464HCID 45480464, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 2-chloro-4-fluoro-5-nitro-benzoic acid (5.0 g, 22.8 mmol) and cesium carbonate (29.7 g, 91.1 mmol) in 2-propanol (100 mL) is heated at 50° C. overnight. The solvent is removed in vacuo and 100 mL of water is added. Concentrated aqueous HCl is added dropwise to this solution at 0° C. until pH=2. The product precipitate which forms is isolated by filtration, washed by water and dried under vacuum to give 2-chloro-4-isopropoxy-5-nitro-benzoic acid.

Workup

  1. customThe solvent is removed in vacuo and 100 mL of water
  2. additionis added
  3. additionConcentrated aqueous HCl is added dropwise to this solution at 0° C. until pH=2
  4. customThe product precipitate which forms is isolated by filtration
  5. washwashed by water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-0615b708448e441ca36aab3d23912d32
Source dataset
uspto-grants-2013_02
Patent number
US08372858B2

Reaction notes

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