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Sodium Bicarbonate → 2,2-dimethyl-4-(3-fluorophenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone

HRID 2298268
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HRID 2298268 반응식
Br[C:2]1[C:3](=[O:19])[C:4]([CH3:18])([CH3:17])[O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+].[F:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:17][C:4]1([CH3:18])[C:3](=[O:19])[C:2]([C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([F:25])[CH:31]=2)=[C:6]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[O:5]1
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7

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HCID 516892Sodium BicarbonateHCID 27339863-Fluorophenylboronic acidHCID 183857274-Bromo-2,2-dimethyl-5-[4-(methylsulfonyl)phenyl]-3(2h)-furanone

생성물 1

HCID 99507622,2-dimethyl-4-(3-fluorophenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone수율 67.6%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 702Ethanol용매
HCID 1140Toluene용매

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온도
90 °C

실험 절차

To a stirred solution of 4-bromo-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone (170 mg) in 30 ml toluene and 10 ml ethanol, were added 25 mg of tetrakis(triphenylphosphine)palladium(0), 10 ml of saturated aqueous sodium bicarbonate, and 100 mg of 3-fluorobenzeneboronic acid. The reaction solution was stirred at 90° C. for 12 hours. Then the solvent was removed under reduced pressure. The resulting residue was extracted with water and dichloromethane. The organic layer was concentrated in vacuo and the resulting residue was separated by column chromatography (hexane/ethylacetate) to yield 120 mg of 2,2-dimethyl-4-(3-fluorophenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone as a solid. mp: 178-179° C. NMR: δ1.58 (s, 6H), 3.08 (s, 3H), 7.05 (m, 3H), 7.33 (m, 1H), 7.83 (d, J=8.7 Hz, 2H), 7.95 (d, J=8.4 Hz, 2H). IR (cm−1): 3020, 1697, 1620, 1403, 1318, 1149, 958, 768. MS (FAB): 361 (m+1).

후처리

  1. customThen the solvent was removed under reduced pressure
  2. extractionThe resulting residue was extracted with water and dichloromethane
  3. concentrationThe organic layer was concentrated in vacuo
  4. customthe resulting residue was separated by column chromatography (hexane/ethylacetate)

출처 및 근거

ORD 기록
ord-0e85534ac5524642ace9f59c4c2ae47d
출처 데이터셋
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06492416B1

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