Hydrochloric Acid → 2-Amino-6-bromo-4-fluoro-3-nitrophenol

HRID 589132Notes

Reaction equation

HRID 589132 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[C:6]([N+:9]([O-])=O)[C:5]([N+:12]([O-:14])=[O:13])=[C:4]([F:15])[CH:3]=1.Cl>CO.O>[NH2:9][C:6]1[C:5]([N+:12]([O-:14])=[O:13])=[C:4]([F:15])[CH:3]=[C:2]([Br:1])[C:7]=1[OH:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 90410240HCID 90410240, compound

Product 1

HCID 904098182-Amino-6-bromo-4-fluoro-3-nitrophenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

6-Bromo-4-fluoro-2,3-dinitrophenol (4.4 g, 16 mmol) was stirred in methanol (88 mL) and 12.0 M hydrogen chloride in water (40 mL), followed by addition of stannous chloride dihydrate (11 g, 47 mmol) and the mixture was stirred at room temperature for 15 min. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was separated and concentrated. Purification on silica gel eluting ethyl acetate in hexanes gave the amine product.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. customPurification on silica gel
  5. washeluting ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a566e1f55c614dc2855a42c62da85f4a
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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