2,6-Lutidine → 4-bromo-1-oxo-2,3-dihydro-1H-inden-5-yl trifluoromethanesulfonate

HRID 2406504노트

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HRID 2406504 반응식
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[Br:16][C:17]1[C:25](O)=[CH:24][CH:23]=[C:22]2[C:18]=1[CH2:19][CH2:20][C:21]2=[O:27].CC1C=CC=C(C)N=1>ClCCl>[Br:16][C:17]1[C:25]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:24][CH:23]=[C:22]2[C:18]=1[CH2:19][CH2:20][C:21]2=[O:27]

참가 물질

5

반응물 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 688667904-Bromo-5-hydroxy-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 867007694-bromo-1-oxo-2,3-dihydro-1H-inden-5-yl trifluoromethanesulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Trifluoromethanesulfonic anhydride (4.0 mL) is added dropwise to a solution of 4-bromo-5-hydroxy-indan-1-one (5.0 g) and 2,6-dimethylpyridine (5.1 mL) in dichloromethane (50 mL) cooled to 0° C. The cooling bath is removed and the mixture is stirred for 2 h at room temperature. The solution is partitioned between saturated aqueous NH4Cl solution and dichloromethane. The organic phase is separated, washed with brine, dried (MgSO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50) to give the title compound. LC (method 2): tR=1.08 min; Mass spectrum (ESI+): m/z=359/361 (Br) [M+H]+.

후처리

  1. customThe cooling bath is removed
  2. customThe solution is partitioned between saturated aqueous NH4Cl solution and dichloromethane
  3. customThe organic phase is separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50)

출처 및 근거

ORD 기록
ord-d7bff5d43bf64878b974949346eeaae3
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809376B2

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