Formaldehyde → 6-Bromo-5-fluoro-2-methylene-2,3-dihydro-1H-inden-1-one

HRID 1468080ノート

反応式

HRID 1468080 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][C:3]=1[F:12].C=O.F[C:16](F)(F)C([O-])=O.C[NH2+]C1C=CC=CC=1>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[CH2:16])[C:8]2=[O:11])=[CH:4][C:3]=1[F:12]

参加物

5

反応物 3

HCID 712FormaldehydeHCID 2724109N-Methylanilinium trifluoroacetateHCID 198011566-Bromo-5-fluoro-2,3-dihydro-1H-inden-1-one

生成物 1

HCID 867066926-Bromo-5-fluoro-2-methylene-2,3-dihydro-1H-inden-1-one収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

6-Bromo-5-fluoro-2,3-dihydro-1H-inden-1-one (commercially available), 4 g, 17.5 mmol), paraformaldehyde (2.48 g, 78.6 mmol) and N-methylanilinium trifluoroacetate (5.79 g, 26.2 mmol) were dissolved in anhydrous THF (80 mL) and refluxed overnight. The mixture was cooled to r.t. and concentrated. The residue was re-dissolved in EtOAc and brine. The phases were separated and the organic phase was dried over sodium sulfate and concentrated. The product was purified by flash column chromatography using heptane/EtOAc 7:1 as eluent affording the title compound (2.99 g, 71% yield). 1H NMR (400 MHz, CDCl3) δ ppm 3.73 (s, 3 H) 5.69 (m, 1 H) 6.39 (m, 1 H) 7.25 (s, 2 H) 8.10 (d, 1 H); MS (EI) m/z 240, 242 M+.

後処理

  1. temperaturerefluxed overnight
  2. concentrationconcentrated
  3. dissolutionThe residue was re-dissolved in EtOAc
  4. customThe phases were separated
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified by flash column chromatography

出典と根拠

ORDレコード
ord-57c38aa1a07946b3959790b4caa4d9fd
出典データセット
uspto-grants-2015_04
特許番号
US09000183B2

反応ノート

読み込み中…