Hydrochloric Acid → 1-Bromo-4-(2-methoxypropan-2-yl)benzene

HRID 1454409

반응식

HRID 1454409 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:12]I.[H-].[Na+].Cl>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:11][CH3:12])([CH3:9])[CH3:10])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 126819202-(4-Bromophenyl)propan-2-ol

생성물 1

HCID 150723851-Bromo-4-(2-methoxypropan-2-yl)benzene수율 27%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-(4-Bromo-phenyl)-propan-2-ol (Preparation 39, 1.77g, 8.2 mmol) and methyl iodide (0.5 mL, 8.2 mmol) in tetrahydrofuran (100 mL) were treated with sodium hydride (60% dispersion in mineral oil, 328 mg, 8.2 mmol). The mixture was stirred for 24 hours at room temperature, was poured into 0.5 M aqueous hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, was dried over magnesium sulfate, was filtered, and the solvent was removed in vacuo. The residue was purified by silica gel chromatography (200:1 hexanes-ethyl acetate) to afford 500 mg (27% yield) of the title compound. 13C NMR (100 MHz, CDCl3) d 145.4, 131.5, 127.9, 121.0, 76.7, 50.9, 28.1; MS (AP/Cl) 197.0, 199.0 (M+H—OMe)+.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialwas dried over magnesium sulfate
  4. filtrationwas filtered
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by silica gel chromatography (200:1 hexanes-ethyl acetate)

출처 및 근거

ORD 기록
ord-c74eba1043ee43c79472346bc0fa9d3e
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07479559B2

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