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Methyl iodide → 5-Bromo-1,2-dimethyl-3-nitrobenzene

HRID 2208910
Notes
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Reaction equation

HRID 2208910 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7](O)=O.C(=O)([O-])[O-].[Na+].[Na+].CI>CN(C=O)C>[CH3:7][C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]=1[CH3:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 137700085-Bromo-2-methyl-3-nitrobenzoic acid

Product 1

HCID 123818655-Bromo-1,2-dimethyl-3-nitrobenzeneYield 119.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 5-bromo-2-methyl-3-nitrobenzoic acid (287 g, 1100 mmol) in DMF (150 mL), were added sodium carbonate (468 g, 4415 mmol) and methyl iodide (627 g, 4415 mmol). The mixture was heated at 60° C. for 8 h. The precipitate was filtered and washed with diethyl ether (5 times). The combined organic layers were dried, concentrated under reduced pressure giving the title compound (302 g, 99%) which was used directly without further purification.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with diethyl ether (5 times)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1b8b8c030ea543b8b0eb36058fca9760
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09376422B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes