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

HRID 391444ノート

反応式

HRID 391444 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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)+.

後処理

  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%)

出典と根拠

ORDレコード
ord-58d7d8776e6f4666b6f7cc8c7a2dad2f
出典データセット
uspto-grants-2013_02
特許番号
US08383821B2

反応ノート

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