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

HRID 519225Notes

Reaction equation

HRID 519225 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[N+:10]([O-])([OH:12])=[O:11].O>C(Cl)Cl>[Br:1][C:2]1[C:3]([F:9])=[CH:4][C:5]([OH:8])=[C:6]([N+:10]([O-:12])=[O:11])[CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 27791534-Bromo-3-fluorophenol

Product 1

HCID 547590604-Bromo-5-fluoro-2-nitrophenolYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. mixture of 4-bromo-3-fluorophenol (70.0 g, 366 mmol) in DCM (500 mL) was added HNO3 (23.0 g, 366 mmol) carefully and the reaction mixture was stirred 30 min. The reaction mixture was poured into water (1 L) and extracted with DCM (3×500 mL). The combined organic portion was washed with brine (300 mL) and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was crystallized from EtOH to give 4-bromo-5-fluoro-2-nitrophenol (42.0 g, 49%). 1H NMR (DMSO-d6, 400 MHz): δ 11.72 (brs, 1H), δ 8.30 (d, J=7.2 Hz, 1H), 7.09 (d, J=10.0 Hz, 1H).

Workup

  1. extractionextracted with DCM (3×500 mL)
  2. washThe combined organic portion was washed with brine (300 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from EtOH

Sources & evidence

ORD record
ord-a1829a7421834c2a9befc2e1306da4fc
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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