N-bromobutanimide → 7-Bromo-5-fluoro-2,3-dihydro-1,4-benzodioxine

HRID 1407521노트

반응식

HRID 1407521 반응식
[F:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O>CO>[Br:12][C:4]1[CH:3]=[C:2]([F:1])[C:11]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:5]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 124645225-Fluoro-2,3-dihydro-1,4-benzodioxine

생성물 1

HCID 686011777-Bromo-5-fluoro-2,3-dihydro-1,4-benzodioxine수율 87.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 5-fluoro-2,3-dihydrobenzo[b][1,4]dioxine (1.54 g, 10.0 mmol) and 1-bromopyrrolidine-2,5-dione (1.8 g, 10 mmol) in methanol (20 mL) was heated at reflux for 0.5 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was taken up in dichloromethane (50 mL) and washed with water (50 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification of the residue by column chromatography eluted with a 0% to 30% gradient of ethyl acetate in hexanes afforded 7-bromo-5-fluoro-2,3-dihydrobenzo[b][1,4]dioxine (2.04 g, 87%) as a colorless solid: MS (ES+) m/z 233.6 (M+1).

후처리

  1. temperatureat reflux for 0.5 h
  2. concentrationconcentrated in vacuo
  3. washwashed with water (50 mL)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by column chromatography
  8. washeluted with a 0% to 30% gradient of ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-2b963be2827845c39bb55a6429131886
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916580B2

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