Water → (7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

HRID 984483

반응식

HRID 984483 반응식
[Br:1][C:2]1[CH:9]=[C:6](C=O)[C:5]([OH:10])=[CH:4][CH:3]=1.[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl.C([O-])([O-])=[O:17].[K+].[K+].O>CN(C=O)C>[OH:17][CH2:14][CH:13]1[CH2:11][O:10][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=2[O:15]1

참가 물질

6

반응물 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

생성물 1

HCID 233965(7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol수율 44%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To a stirred solution of 5-bromosalicylaldehyde (5.0 g, 24.9 mmol), and epichlorohydrin (5.6 mL, 72.1 mmol) in 20 mL of DMF at 80° C. was added K2CO3 slowly in portions. The resulting mixture was then heated at 90° C. for 3 h. Reaction was then stopped, water was added, extracted with diethyl ether. The organic extracts were washed with water, brine, dried over Na2SO4, concentrated in vacuo. The residue was purified on a SiO2 flash column chromatography eluting with 15-30% EtOAc/hexanes to give 2.82 g (44%) of the title compound as colorless oil.

후처리

  1. customReaction
  2. extractionextracted with diethyl ether
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on a SiO2 flash column chromatography
  7. washeluting with 15-30% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-1dc99065235e46769bedd783d4257b57
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867203B2

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