HCID 90410240, compound → 2-Amino-6-bromo-4-fluoro-3-nitrophenol

HRID 928552Notes

Reaction equation

HRID 928552 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>CO.Cl.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 1

HCID 90410240HCID 90410240, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 6-bromo-4-fluoro-2,3-dinitrophenol (4.4 g, 16 mmol) in methanol (88 mL) and 12.0 M hydrogen chloride in water (40 mL) was added stannous chloride, dihydrate (11 g, 47 mmol). The reaction was stirred at RT for 15 min. Water was added and the mixture was extracted with ethyl acetate. The organic layer was separated and concentrated. Purification on silica gel using ethyl acetate in hexanes gave the desired compound, 2.48 g, 63%. 1H NMR (300 MHz, DMSO-d6) δ 9.80 (br s, 3H), 6.80 (m, 1H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. customPurification on silica gel

Sources & evidence

ORD record
ord-948fb2490ca34717aa36d6b648892bfe
Source dataset
uspto-grants-2016_03
Patent number
US09290514B2

Reaction notes

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