Tetrahydrofuran → (5-Bromo-2-chloro-3-methoxyphenyl)(4-ethylphenyl)methanone

HRID 576333노트

반응식

HRID 576333 반응식
[Br:1][C:2]1[CH:3]=[C:4]([O:15][CH3:16])[C:5]([Cl:14])=[C:6]([CH:13]=1)[C:7](N(OC)C)=[O:8].C(O[C:20]1[CH:25]=[CH:24][C:23]([Mg]Br)=[CH:22][CH:21]=1)C.[CH2:28]1COC[CH2:29]1>>[Br:1][C:2]1[CH:3]=[C:4]([O:15][CH3:16])[C:5]([Cl:14])=[C:6]([C:7]([C:20]2[CH:21]=[CH:22][C:23]([CH2:28][CH3:29])=[CH:24][CH:25]=2)=[O:8])[CH:13]=1

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 867140445-Bromo-2-chloro-N,3-dimethoxy-N-methylbenzamideHCID 178466691HCID 178466691, 화합물

생성물 1

HCID 71110682(5-Bromo-2-chloro-3-methoxyphenyl)(4-ethylphenyl)methanone수율 99%

실험 절차

To a solution of compound 60 (3.45 g, 11.2 mmol) in THF (44 mL) was added dropwise 4-ethoxyphenyl magnesium bromide (0.5M in THF, 44.8 mL, 22.4 mmol) at 0° C. under an atmosphere of nitrogen. After being stirred for 15 hours at room temperature, the mixture was quenched with 1N HCl (10 mL). The mixture was extracted with EtOAc (100 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the product 61 (3.92 g, 99%) as a white solid.

후처리

  1. customthe mixture was quenched with 1N HCl (10 mL)
  2. extractionThe mixture was extracted with EtOAc (100 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-287b1cf985ce4132af5a6cde7821c7d2
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034921B2

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