Acetonitrile → (4-Bromo-2-chloro-phenyl)-(2-fluoro-5-hydroxy-phenyl)-methanone

HRID 1012654ノート

反応式

HRID 1012654 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[C:14]([O:16][Si](C(C)(C)C)(C)C)[CH:13]=[CH:12][C:11]=2[F:24])[OH:9])=[C:4]([Cl:25])[CH:3]=1.C(#N)C.C[N+]1([O-])CCOCC1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:11]=2[F:24])=[O:9])=[C:4]([Cl:25])[CH:3]=1

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 82029Methyl morpholine oxideHCID 67314496(4-Bromo-2-chloro-phenyl)-[5-(tert-butyl-dimethyl-silanyloxy)-2-fluoro-phenyl]-methanol

生成物 1

HCID 67314566(4-Bromo-2-chloro-phenyl)-(2-fluoro-5-hydroxy-phenyl)-methanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Compound 510 (15.9 g, 35.6 mmol) was dissolved in dry DCM (80 mL) and dry acetonitrile (10 mL) under an argon atmosphere. The mixture was cooled to 0° C. and added 4-methyl-morpholine 4-oxide (6.27 g, 53.5 mmol), grinded molecular sieve (4 Å, 17.8 g). Tetra-N-propylammonium perruthenate (VII) (250 mg, 0.71 mmol) was added in 5 portions (5×50 mg) and the reaction mixture was stirred for 10 min. at 0° C., evaporated to ⅓ volume and filtered through silica. The silica was washed with EtOAc (300 mL). The organic phase was concentrated in vacuo affording the crude product. Purified by continuously gradient flash chromatography using EtOAc/petroleum ether (40-60)(v:v=1:80 to 1:10) as the eluent, affording the title compound as a yellow solid.

後処理

  1. customgrinded molecular sieve (4 Å, 17.8 g)
  2. customevaporated
  3. filtrationfiltered through silica
  4. washThe silica was washed with EtOAc (300 mL)
  5. concentrationThe organic phase was concentrated in vacuo
  6. customaffording the crude product
  7. customPurified by continuously gradient flash chromatography

出典と根拠

ORDレコード
ord-18ace6b616174ab490382786a796dde7
出典データセット
uspto-grants-2011_07
特許番号
US07977387B2

反応ノート

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