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Sodium Carbonate → HCID 21099398、化合物

HRID 1351646
ノート
印刷プレビュー

反応式

HRID 1351646 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 21099496HCID 21099496、化合物HCID 86225520HCID 86225520、化合物

生成物 1

HCID 21099398HCID 21099398、化合物収率 69%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-344dc13c43634366b185bb207fd254b7
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07217740B2

反応ノート

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