1,2-Dibromoethane → 8-Bromo-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde

HRID 15324

반응식

HRID 15324 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][CH2:20]Br>CN(C)C=O>[Br:1][C:2]1[C:9]2[O:10][CH2:19][CH2:20][O:11][C:8]=2[CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1

참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 854055-Bromo-3,4-dihydroxybenzaldehyde

생성물 1

HCID 166371768-Bromo-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde수율 75%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-bromo-4,5-dihydroxybenzaldehyde (11.5 g, 0.52 mol) in dimethylformamide (220 ml) was added cesium carbonate (50.7 g, 1.56 mol). The mixture was stirred at ambient temperature for 30 min, then 1,2-dibromoethane (12.76 g, 0.68 mol) were added. After heating at 80° for 4 h, the dimethylformamide was removed under reduced pressure. The residue was partitioned between water and ethyl acetate, and the organic layer was washed with brine and dried. The crude product was purified by flash column chromatography (silica gel, 4:1 hexane:ethyl acetate) to give the desired compound as an off-white solid (9.57 g, 75%).

후처리

  1. temperatureAfter heating at 80° for 4 h
  2. customthe dimethylformamide was removed under reduced pressure
  3. customThe residue was partitioned between water and ethyl acetate
  4. washthe organic layer was washed with brine
  5. customdried
  6. customThe crude product was purified by flash column chromatography (silica gel, 4:1 hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-1485c067dc3942858e5d7f74b0bdc26e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732461B2

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