Diethyl Ether → 2-[2-Fluoro-4-(furan-2-ylmethyl)-phenyl]propionic acid

HRID 1506870노트

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HRID 1506870 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:14])[C:10]([O:12]C)=[O:11])=[C:5]([F:15])[CH:4]=1.[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].CCOCC>O1CCCC1.C1C(=O)[N-]C(=O)C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Br[Pd+]>[F:15][C:5]1[CH:4]=[C:3]([CH2:2][C:17]2[O:16][CH:20]=[CH:19][CH:18]=2)[CH:8]=[CH:7][C:6]=1[CH:9]([CH3:14])[C:10]([OH:12])=[O:11]

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 49837497Methyl 2-[4-(bromomethyl)-2-fluorophenyl]-propionate

생성물 1

HCID 601555312-[2-Fluoro-4-(furan-2-ylmethyl)-phenyl]propionic acid수율 45.3%

시약·촉매·용매 2

HCID 11434313trans-Bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II)촉매HCID 8028Tetrahydrofuran용매

실험 절차

Compound 20 (0.88 g, 3.2 mmol) and 2-furan boronic acid (0.54 g, 4.8 mmol) were dissolved in tetrahydrofuran (12 mL) and a 2 M-aqueous solution (4.0 mL) of sodium carbonate. To this solution, trans-bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II) [trans-PdBr(N-Succ)(PPh3)2] (25.9 mg, 1.0 mol %) was added and heated to reflux for 3 hours. After cooling to room temperature and adding ether (50 mL) to the solution, the organic layer was washed with water (30 mL) and dried (over magnesium sulfate), and the solvent was distilled off. The obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (20:1) solution followed by conventional hydrolysis with potassium hydroxide to give 0.36 g (43%) of compound (21a) of interest as white solid.

후처리

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. washthe organic layer was washed with water (30 mL)
  4. dry with materialdried (over magnesium sulfate)
  5. distillationthe solvent was distilled off
  6. washThe obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (20:1) solution
  7. customfollowed by conventional hydrolysis with potassium hydroxide

출처 및 근거

ORD 기록
ord-7b87ed0f4bce44fe83e2308b9d64daad
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221786B2

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