Hydrochloric Acid → Phenol, 2-chloro-4-fluoro-5-nitro-

HRID 1826257Notes

Reaction equation

HRID 1826257 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:9]([O:10]C(OC)=O)=[CH:8][C:7]([N+:15]([O-:17])=[O:16])=[C:6]([F:18])[CH:5]=1.Cl>CO>[Cl:3][C:4]1[C:9]([OH:10])=[CH:8][C:7]([N+:15]([O-:17])=[O:16])=[C:6]([F:18])[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 37866902-Chloro-4-fluoro-5-nitrophenyl methyl carbonate

Product 1

HCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-Yield 96.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

A 6N aqueous sodium hydroxide solution (17 ml) was added dropwise to a stirred solution of 4-chloro-2-fluoro-5-methoxycarbonyloxy-1-nitrobenzene (J. Med. Chem., 1999, 42, 5369; 25 g) in methanol (200 ml) which was cooled to 5° C. The reaction mixture was stirred at ambient temperature for 30 minutes. A 12N aqueous hydrochloric acid solution (8.5 ml) was added and the mixture was evaporated. The residue was partitioned between methylene chloride and water. The organic layer was washed with brine, dried over magnesium sulphate and evaporated to give 4-chloro-2-fluoro-5-hydroxy-1-nitrobenzene (18.5 g); NMR Spectrum: (CDCl3) 5.8 (br s, 1H), 7.35 (d, 1H), 7.75 (d, 1H).

Workup

  1. customthe mixture was evaporated
  2. customThe residue was partitioned between methylene chloride and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-db366b8a264e45a982973efd39849654
Source dataset
uspto-grants-2006_05
Patent number
US07049438B2

Reaction notes

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