Potassium Carbonate → Benzyl 3-((8-(1,3-dioxolan-2-yl)octyl)oxy)-5-bromobenzoate

HRID 332658

반응식

HRID 332658 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([OH:18])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]1[O:32][CH2:31][CH2:30][O:29]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[O:29]1[CH2:30][CH2:31][O:32][CH:28]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:18][C:16]1[CH:15]=[C:4]([CH:3]=[C:2]([Br:1])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 118323182-(8-Bromooctyl)-1,3-dioxolaneHCID 71093147Benzyl 3-bromo-5-hydroxybenzoate

생성물 1

HCID 71093165Benzyl 3-((8-(1,3-dioxolan-2-yl)octyl)oxy)-5-bromobenzoate수율 65%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of benzyl 3-bromo-5-hydroxybenzoate (2.85 g, 9.22 mmol) in dimethyl formamide (50 mL), was added 2-(8-bromooctyl)-1,3-dioxolane (2.44 g, 9.21 mmol) and potassium carbonate (1.91 g, 13.8 mmol), and the mixture stirred at 80° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried (magnesium sulphate), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-7% ethyl acetate in iso-hexane to afford the title compound (2.94 g, 65%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with 0-7% ethyl acetate in iso-hexane

출처 및 근거

ORD 기록
ord-a8db384a0f6442fc9796af4e01bd80d0
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877774B2

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