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Lithium hydroxide, monohydrate → HCID 67393208, 화합물

HRID 1776938
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HRID 1776938 반응식
[Br:1][C:2]1[C:3]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]([O:19]CC)=[O:18])[C:6]=2[CH:22]=1.O[Li].O>O1CCOCC1.O>[Br:1][C:2]1[C:3]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]([OH:19])=[O:18])[C:6]=2[CH:22]=1
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참가 물질

4

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 67393727HCID 67393727, 화합물

생성물 1

HCID 67393208HCID 67393208, 화합물수율 96%

시약·촉매·용매 1

HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
100 °C

실험 절차

To a solution of ethyl 5-bromo-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylate (53 g, 0.23 mol) in dioxane/H2O (5/1, 600 mL) was added LiOH.H2O (25 g, 1.17 mol), and the mixture was stirred at 100° C. for 3 hours. After concentrated, the resulting residue was dissolved in H2O, 1 N HCl was added until pH reached 3, and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and filtered. The solvent was removed to provide the product of 5-bromo-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylic acid (48 g, yield: 96%). 1H-NMR (DMSO-d6, 400 MHz) δ 13.49 (s, 1H), 9.67 (s, 1H), 8.30 (s, 1H), 8.12˜8.17 (m, 2H), 7.87 (s, 1H), 7.45˜7.50 (m, 2H), 3.16 (s, 3H). MS (M+H)+: 428/430.

후처리

  1. concentrationAfter concentrated
  2. dissolutionthe resulting residue was dissolved in H2O
  3. addition1 N HCl was added until pH
  4. extractionthe mixture was extracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customThe solvent was removed

출처 및 근거

ORD 기록
ord-29b44f24f2974894b64b885764288f5b
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09265773B2

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