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

HRID 1373270Notes

Reaction equation

HRID 1373270 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-ebf4952391e1494e9b54fb5c3cb0de5a
Source dataset
uspto-grants-2007_01
Patent number
US07160891B2

Reaction notes

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