N-bromobutanimide → 4-bromo-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one

HRID 1798671노트

반응식

HRID 1798671 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11](=[O:16])[CH:10]=2)=[CH:5][CH:4]=1.C1C(=O)N([Br:24])C(=O)C1>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:24][C:10]1[C:11](=[O:16])[C:12]([CH3:14])([CH3:15])[O:13][C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 145333195-(4-Methoxyphenyl)-2,2-dimethylfuran-3(2H)-one

생성물 1

HCID 593547994-bromo-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one수율 65%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (5.5 g, 0.025 mol) in CHCl3 (100 mL) was added NBS (6.733 g, 0.038 mol) portion wise at RT. The reaction mixture was stirred for 2 h at RT. The reaction mixture was diluted with DCM (100 mL), washed with water (50 mL), brine (50 mL), dried over Na2SO4, filtered and then concentrated in vacuo to obtain the crude product. The crude material was purified via by flash column chromatography using 25% ethyl acetate in hexane and silica gel (230-400 Mesh) to afford 4-bromo-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (4.6 g, 65%) as a solid.

후처리

  1. washwashed with water (50 mL), brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto obtain the crude product
  6. customThe crude material was purified via by flash column chromatography

출처 및 근거

ORD 기록
ord-460046285efa417ca5b6774933c605bf
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343973B2

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