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

HRID 1468080노트

반응식

HRID 1468080 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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+.

후처리

  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

출처 및 근거

ORD 기록
ord-57c38aa1a07946b3959790b4caa4d9fd
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000183B2

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