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

HRID 491725Notes

Reaction equation

HRID 491725 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1.C([O-])(=O)C.[Na+].S(=O)(=O)(O)O>C(O)(=O)C.O>[Br:1][C:9]1[CH:10]=[C:5]([O:4][CH3:3])[CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[C:8]=1[OH:11]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 15285Phenol, 4-methoxy-2-nitro-HCID 24408BromineHCID 517045Sodium Acetate

Product 1

HCID 112651402-Bromo-4-methoxy-6-nitrophenol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

Bromine (16.0 g, 100 mmol) in acetic acid (20 mL) was added into a mixture of 4-methoxy-2-nitrophenol (16.9 g, 100 mmol, sodium acetate (16.4 g, 200 mmol) and acetic acid (100 mL). The mixture was stirred for 30 min at room temperature, and then at 70° C. for 2 h and poured into water (1.5 l) containing concentrated sulfuric acid (10 mL). The precipitated solid filtered and crystallized from (chloroform/hexane) to give a brownish solid, m.p. 116-118° C.; MS m/e 246 (M−H)+.

Workup

  1. waitat 70° C. for 2 h
  2. filtrationThe precipitated solid filtered
  3. customcrystallized from (chloroform/hexane)
  4. customto give a brownish solid, m.p. 116-118° C.

Sources & evidence

ORD record
ord-11fdb86adf5a4335a2213406433879fd
Source dataset
uspto-grants-2009_05
Patent number
US07531564B2

Reaction notes

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