Ammonium Chloride → 2-Amino-4-bromo-5-fluorophenol

HRID 519226Notes

Reaction equation

HRID 519226 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.[Cl-].[NH4+]>CO.C1COCC1.[Zn]>[NH2:10][C:4]1[CH:3]=[C:2]([Br:1])[C:7]([F:8])=[CH:6][C:5]=1[OH:9]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 547590604-Bromo-5-fluoro-2-nitrophenol

Product 1

HCID 383722992-Amino-4-bromo-5-fluorophenolYield 109.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-5-fluoro-2-nitrophenol (40.0 g, 169 mmol) in MeOH (250 mL) and THF (250 mL) was added zinc powder (91.0 g, 1700 mmol) and ammonium chloride (111.0 g, 1700 mmol) and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was washed with cold water to give 2-amino-4-bromo-5-fluorophenol (38.0 g, crude) which was used in the next step directly without further purification. 1H NMR (DMSO-d6, 400 MHz): δ 9.82 (br s, 1H), δ 6.76 (d, J=7.2 Hz, 1H), 6.60 (d, J=10.0 Hz, 1H), 4.65 (br s, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. washThe residue was washed with cold water

Sources & evidence

ORD record
ord-464d4b35829c4d1c86b0eefba09e1502
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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