Water → 1-Bromo-2-methoxy-3-nitrobenzene

HRID 272779

Reaction equation

HRID 272779 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[OH:11].[H-].[Na+].I[CH3:15].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[O:11][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 135454532-Bromo-6-nitrophenol

Product 1

HCID 225057131-Bromo-2-methoxy-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-6-nitrophenol (5.1 g, 23.4 mmol) was dissolved in DMF (60 mL), then 95% NaH (900 mg, 35.6 mmol) was added in a few portions, followed by the addition of iodomethane (3.0 mL, 6.8 g, 48.5 mmol). The reaction was stirred at room temperature overnight, then heated at 50° C. for 3 hours. The reaction was cooled, poured into water, and the solids filtered off and dried. The product (5.5 g, 100%) was recovered as tan solids. 1H NMR (300 MHz, DMSO-d6) δ 8.02 (dd, J=8.1, 1.7 Hz, 1H), 7.96 (dd, J=8.1, 1.7 Hz, 1H), 7.83 (dd, 8.1, 8.1 Hz, 1H), 3.92 (s, 3H).

Workup

  1. temperatureheated at 50° C. for 3 hours
  2. temperatureThe reaction was cooled
  3. filtrationthe solids filtered off
  4. customdried
  5. customThe product (5.5 g, 100%) was recovered as tan solids

Sources & evidence

ORD record
ord-d03ed043ac1a41c886c1001eaa0187a2
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Linked notes

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