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

HRID 391444

반응식

HRID 391444 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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)+.

후처리

  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%)

출처 및 근거

ORD 기록
ord-58d7d8776e6f4666b6f7cc8c7a2dad2f
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383821B2

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