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

HRID 460311

반응식

HRID 460311 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].[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

참가 물질

6

반응물 4

HCID 962WaterHCID 3024DibromomethaneHCID 854055-Bromo-3,4-dihydroxybenzaldehydeHCID 522689Potassium Fluoride

생성물 1

HCID 23202437-Bromo-1,3-dioxaindane-5-carbaldehyde수율 60.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-0d38999cde49444faa0534a1045bfd1b
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196108B2

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