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

HRID 641718Notes

Reaction equation

HRID 641718 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-84f843c42bd943aa836dfd3b6baece80
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

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