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

HRID 2406504ノート

反応式

HRID 2406504 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-d7bff5d43bf64878b974949346eeaae3
出典データセット
uspto-grants-2014_08
特許番号
US08809376B2

反応ノート

読み込み中…