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

HRID 38379

反応式

HRID 38379 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.[K+].[K+].Br[CH2:19][CH2:20]Br.O>CN(C=O)C>[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

6

反応物 4

HCID 962WaterHCID 78391,2-Dibromoethane2 回HCID 11430Potassium CarbonateHCID 854055-Bromo-3,4-dihydroxybenzaldehyde

生成物 1

HCID 166371768-Bromo-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde収率 99%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-bromo-4,5-dihydroxy-benzaldehyde (20.78 g, 95 mmol) in 480 ml DMF was added K2CO3 (52.95 g, 383 mmol) followed by 1,2-dibromoethane (8.7 ml, 101 mmol). The mixture was warmed to 100° C. After 18 additional 1,2 dibromoethane (1.0 mL) was added. After 2 h the mixture was poured into water and extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude solid was purified via flash chromatography (9:1 hexane/ethyl acetate) to give 8-bromo-2,3-dihydro-benzo[1,4]dioxine-6-carboxaldehyde (15.82 g, 99%) as a white solid.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude solid was purified via flash chromatography (9:1 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-a09ae0eeec814451a55c3ee672c1fdc6
出典データセット
uspto-grants-2013_09
特許番号
US08524725B2

関連ノート

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