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

HRID 2206706ノート

反応式

HRID 2206706 の反応式
[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

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 867140445-Bromo-2-chloro-N,3-dimethoxy-N-methylbenzamideHCID 178466691HCID 178466691、化合物

生成物 1

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

実験手順

To a solution of compound 60 (3.45 g, 11.2 mmol) in THF (44 mL) was added dropwise 4-ethoxyphenyl magnesium bromide (0.5 M 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 1 N 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.

後処理

  1. customthe mixture was quenched with 1 N 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

出典と根拠

ORDレコード
ord-b2598ae00031424a9671b75d4adf6c6f
出典データセット
uspto-grants-2016_06
特許番号
US09371303B2

反応ノート

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