Bromine → 4-Bromo-2-methoxy-6-methylaniline

HRID 2427494Notes

Reaction equation

HRID 2427494 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[NH2:10].[Br:11]Br>CO.C(O)(=O)C>[Br:11][C:7]1[CH:6]=[C:5]([CH3:9])[C:4]([NH2:10])=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 4592492-Methoxy-6-methylaniline

Product 1

HCID 106802184-Bromo-2-methoxy-6-methylanilineYield 87%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent

Procedure

2-Methoxy-6-methyl phenylamine (10 g, 72.9 mmol) was set stirring in methanol (30 mL) and acetic acid (10 mL) at 0° C. Bromine (3.73 mL, 72.9 mmol) was dissolved in acetic acid (15 mL) and added dropwise to the reaction. The reaction was stirred for 2 hours and the solvent was removed under reduced pressure. The resulting residue was basified with 1N NaOH and partitioned with EtOAc. The organic layer was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the product was purified by column chromatography (20% EtOAc/Hexanes) to afford a red-brown solid (6.86 g, 87%). 1H NMR (300 MHz, CDCl3): δ 6.87 (d, 1H), 6.81 (d, 1H), 3.85 (s, 3H), 2.16 (s, 3H).

Workup

  1. customat 0° C
  2. additionadded dropwise to the reaction
  3. customthe solvent was removed under reduced pressure
  4. custompartitioned with EtOAc
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customthe product was purified by column chromatography (20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-a47affc248004d0a81bf9ac97239b1ab
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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