Dimethylformamide → Methyl 5-bromo-2-methoxy-3-methylbenzoate

HRID 391444

Reaction equation

HRID 391444 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5](O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].IC.[C:15](=O)([O-])[O-].[K+].[K+].CN(C)[CH:23]=[O:24]>>[Br:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([O:24][CH3:23])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:15])=[O:8]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27643455-Bromo-2-hydroxy-3-methylbenzoic acid

Product 1

HCID 2764346Methyl 5-bromo-2-methoxy-3-methylbenzoate

Procedure

5-Bromo-2-hydroxy-3-methylbenzoic acid (2.8 g, 12.1 mmol), iodomethane (1.97 mL, 31.6 mmol) and potassium carbonate (16.9 g, 123 mmol) were combined in dimethylformamide (30 mL). After stirring at room temperature for 16 h, the solvent was removed in vacuo and the crude product dissolved in ethyl acetate, which was washed with water (2×), then brine (2×), dried over sodium sulfate, and concentrated. Flash chromatography on silica gel (10% ethyl acetate/hexanes) gave 2.26 g (72%). 1H-NMR (CDCl3, 500 MHz) δ 7.74-7.75 (m, 1H), 7.45-7.46 (m, 1H), 3.90 (s, 3H), 3.80 (s, 3H), 2.28 (s, 3H). Mass spec.: 261.08 (MH)+.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe crude product dissolved in ethyl acetate
  3. washwhich was washed with water (2×)
  4. dry with materialbrine (2×), dried over sodium sulfate
  5. concentrationconcentrated
  6. customFlash chromatography on silica gel (10% ethyl acetate/hexanes) gave 2.26 g (72%)

Sources & evidence

ORD record
ord-58d7d8776e6f4666b6f7cc8c7a2dad2f
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Linked notes

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