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Sodium Carbonate → HCID 21099398, 화합물

HRID 2376961
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HRID 2376961 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)(=[O:10])=[O:9].[F:19][C:20]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:21]=1[CH2:22]P(=O)(OC)OC.C1OCCOCCOCCOCCOC1.[H-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C:11]1[CH:18]=[CH:17][C:14](/[CH:15]=[CH:22]/[C:21]2[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:20]=2[F:19])=[CH:13][CH:12]=1)(=[O:10])=[O:9]
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참가 물질

8

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HCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 21099496HCID 21099496, 화합물HCID 86225520HCID 86225520, 화합물

생성물 1

HCID 21099398HCID 21099398, 화합물수율 69%

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

4-[(2-bromophenyl)sulfonyl]benzaldehyde (Step 4, 3.4 g, 10 46 mmol), dimethyl (2,4-difluorobenzyl)phosphonate (2.36 g, 11.51 mmol) and 15-crown-5 (0.23 mL, 1.15 mmol) were dissolved in tetrahydrofuran (21 mL) under nitrogen and cooled to 0° C. Sodium hydride (276 mg) was added and the reaction allowed to warm slowly to room temperature. Saturated sodium carbonate solution and ethyl acetate were added. The organic layer was washed with brine, dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 35% ethyl acetate/isohexane, to give 1-((E)-2-{4-[(2-bromophenyl)sulfonyl]phenyl}vinyl)-2,4-difluorobenzene as a white solid (3.1 g, 69%). δH (400 MHz, d6 DMSO): 8.33 (1H, dd, J=1.7, 7.9 Hz), 7.89-7.81 (6H, m), 7.72 (1H, td, J=1.2, 7.6 Hz), 7.62 (1H, td, J=1.8, 7.6 Hz), 7.45-7.35 (2H, m), 7.33-7.29 (1H, m), 7.16 (1H, td, J=2.5, 8.3 Hz).

후처리

  1. temperatureto warm slowly to room temperature
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with 35% ethyl acetate/isohexane

출처 및 근거

ORD 기록
ord-8646f664f1c84805b5a1cf8dd603c23f
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07468393B2

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