Dimethylformamide → 5-Fluoro-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

HRID 1943238노트

반응식

HRID 1943238 반응식
Br[C:2]1[CH:11]=[CH:10][C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[C:3]=1[F:12].[Li]CCCC.CN([CH:21]=[O:22])C>C1COCC1>[F:12][C:3]1[C:4]2[O:9][CH2:8][CH2:7][O:6][C:5]=2[CH:10]=[CH:11][C:2]=1[CH:21]=[O:22]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 124645241,4-Benzodioxin, 6-bromo-5-fluoro-2,3-dihydro-HCID 178418339Butyllithium

생성물 1

HCID 866421125-Fluoro-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde수율 22%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

A solution of 6-bromo-5-fluoro-2,3-dihydro-1,4-benzodioxin (146 mg, 0.627 mmol) in THF (5 ml) at −78° C. was treated with n-BuLi (0.551 ml, 1.378 mmol) under a nitrogen atmosphere and stirred at −78° C. for 15 min before treatment with a solution of DMF (0.243 ml, 3.13 mmol) in THF) (2.00 ml). The reaction was stirred for 10 min at −78° C. and then the reaction was allowed warm to rt over 10 min and stirred at rt for 0.5 h. Reaction was treated with 2M HCl (20 ml) and extracted with ethyl acetate (3×100 ml). The organic extracts were evaporated, dried (MgSO4), filtered, evaporated, chromatographed (0-100% EtOAC:Cyclohexane) to give product as a white solid (25 mg, 22%).

후처리

  1. temperaturethe reaction was allowed warm to rt over 10 min
  2. stirringstirred at rt for 0.5 h
  3. customReaction
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. customThe organic extracts were evaporated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customchromatographed (0-100% EtOAC:Cyclohexane)

출처 및 근거

ORD 기록
ord-6c56a9e2edb34fceaa0c6566e8b08525
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389524B2

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