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

HRID 15324

反応式

HRID 15324 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-1485c067dc3942858e5d7f74b0bdc26e
出典データセット
uspto-grants-2010_06
特許番号
US07732461B2

関連ノート

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