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

HRID 1407521ノート

反応式

HRID 1407521 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2b963be2827845c39bb55a6429131886
出典データセット
uspto-grants-2014_12
特許番号
US08916580B2

反応ノート

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