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

HRID 576333ノート

反応式

HRID 576333 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 (0.5M 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.

後処理

  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

出典と根拠

ORDレコード
ord-287b1cf985ce4132af5a6cde7821c7d2
出典データセット
uspto-grants-2015_05
特許番号
US09034921B2

反応ノート

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