Hydrochloric Acid → 2-Bromo-4-methoxy-6-nitrophenol

HRID 1824786Notes

Reaction equation

HRID 1824786 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.CC(O[Na])=O.[Br:18]Br.Cl>C(O)(=O)C.C(OCC)(=O)C>[Br:18][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6]=1[OH:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 15285Phenol, 4-methoxy-2-nitro-HCID 24408Bromine2×HCID 178418247HCID 178418247, compound

Product 1

HCID 112651402-Bromo-4-methoxy-6-nitrophenolYield 60%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-Methoxy-2-nitro-phenol (10 g) was dissolved in glacial acetic acid (60 mL) and CH3CO2Na (8.2 g) was added. Next, bromine (3 mL) dissolved in glacial acetic acid (12 mL) was added drop wise to the stirring solution at room temperature. After complete addition of bromine, the mixture was stirred for 30 min at room temperature and then placed in an oil bath at 75° C. for 2 h. After reaction mixture cooled to room temperature, concentrated HCl (500 mL) was slowly added to the mixture followed by addition of ethyl acetate (500 mL). The layers were separated and the organic layer was washed with water, brine, dried (Na2SO4). Flash chromatography on silica gel eluting with 5% ethyl acetate-hexane afforded 8.8 g (60%) of the title compound as a solid. MS: 218 (MH+−30), HPLC tR: 2.40 min.

Workup

  1. additionwas added drop wise to the stirring solution at room temperature
  2. waitplaced in an oil bath at 75° C. for 2 h
  3. customAfter reaction mixture
  4. temperaturecooled to room temperature
  5. customThe layers were separated
  6. washthe organic layer was washed with water, brine
  7. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-b32e55a478f941e0871a4c11f4c6d843
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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