Hydrochloric Acid → 2-Bromo-4-fluoro-5-nitrophenol

HRID 2404881Notes

Reaction equation

HRID 2404881 reaction equation
C(=O)(OC)[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([F:12])=[CH:5][C:4]=1[Br:13].[OH-].[K+].Cl>CO>[Br:13][C:4]1[CH:5]=[C:6]([F:12])[C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[OH:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13268178Methyl 2-bromo-4-fluoro-5-nitrophenoxyformate

Product 1

HCID 132681792-Bromo-4-fluoro-5-nitrophenolYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-bromo-4-fluoro-5-nitrophenyl methyl carbonate (8.90 g, 30.27 mmol) in methanol (100 mL) was added KOH (4.25 g, 75.68 mmol) portionwise at 0° C. After the addition was complete the reaction mixture was allowed to warm to room temperature and stirred for 1.5 h. The reaction mixture was acidified by 1N HCl. The solvent was evaporated and water was added. The aqueous layer was extracted with DCM (3×10 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated to give 2-bromo-4-fluoro-5-nitro-phenol (7.05 g, 99%). 1H NMR (400 MHz, CDCl3) δ 7.75 (d, J=6.6 Hz, 1H), 7.51 (d, J=9.6 Hz, 1H), 5.62 (s, 1H).

Workup

  1. additionAfter the addition
  2. customThe solvent was evaporated
  3. additionwater was added
  4. extractionThe aqueous layer was extracted with DCM (3×10 mL)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-06241e9e9dce40d09d41757617398c16
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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