Sodium Hydroxide → 2-Bromo-4-fluoro-5-nitrophenol

HRID 1018436Notes

Reaction equation

HRID 1018436 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]([F:13])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:3]=1[O:4]C(OC)=O.[OH-].[Na+]>O>[Br:1][C:2]1[CH:12]=[C:11]([F:13])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:3]=1[OH:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13268178Methyl 2-bromo-4-fluoro-5-nitrophenoxyformate

Product 1

HCID 132681792-Bromo-4-fluoro-5-nitrophenolYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Then, 125 g (0.43 mol) of methyl 2-bromo-4-fluoro-5-nitrophenoxyformate was suspended in 200 ml of water, to which 19 g (0.47 mol) of sodium hydroxide was added, and the mixture was stirred at 50° to 60° C. for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and washed with chloroform. The aqueous layer was acidified with aqueous hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was dried and concentrated, which afforded 104 g (0.43 mol) of 2-bromo-4-fluoro-5-nitrophenol.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. washwashed with chloroform
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f6498ea0c99f4fa2a83aef8b5553da76
Source dataset
uspto-grants-2002_11
Patent number
US06482773B1

Reaction notes

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