Water → 7-Bromo-1,3-dioxaindane-5-carbaldehyde

HRID 460311

反応式

HRID 460311 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].[F-].[K+].Br[CH2:15]Br.O>CN(C=O)C>[Br:1][C:2]1[C:9]2[O:10][CH2:15][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 3024DibromomethaneHCID 854055-Bromo-3,4-dihydroxybenzaldehydeHCID 522689Potassium Fluoride

生成物 1

HCID 23202437-Bromo-1,3-dioxaindane-5-carbaldehyde収率 60.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

To a solution of 3-bromo-4,5-dihydroxy-benzaldehyde (1.52 g, 7.02 mmol) in DMF (20 mL), were added KF (4.077 g, 70.18 mmol) followed by dibromomethane (1 mL, 14.04 mmol) and the mixture heated at 140° C. for 4 hours. The solution was cooled to room temperature, water was added and the mixture extracted with ether. The organic layer was further washed with saturated aqueous NaHCO3, dried (MgSO4), filtered and evaporated to give 973 mg of 7-bromo-benzo[1,3]dioxole-5-carbaldehyde. 1H NMR (300 MHz; CDCl3): δ 6.16 (s, 2H), 7.26 (s, 1H), 7.54 (s, 1H), 9.76

後処理

  1. temperatureThe solution was cooled to room temperature
  2. extractionthe mixture extracted with ether
  3. washThe organic layer was further washed with saturated aqueous NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-0d38999cde49444faa0534a1045bfd1b
出典データセット
uspto-grants-2007_03
特許番号
US07196108B2

関連ノート

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