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

HRID 38379

반응식

HRID 38379 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.[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

참가 물질

6

반응물 4

HCID 962WaterHCID 78391,2-Dibromoethane2회HCID 11430Potassium CarbonateHCID 854055-Bromo-3,4-dihydroxybenzaldehyde

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a09ae0eeec814451a55c3ee672c1fdc6
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524725B2

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