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

HRID 1012654

반응식

HRID 1012654 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-18ace6b616174ab490382786a796dde7
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977387B2

연결된 노트

불러오는 중…