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Formic Acid → 5-(4-Fluoro-benzoyl)-2-methylsulfonylnaphthalene

HRID 1858006
ノート
印刷プレビュー

反応式

HRID 1858006 の反応式
[F:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([C:8]2[C:17](OS(C(F)(F)F)(=O)=O)=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:13]3)=[O:7])=[CH:4][CH:3]=1.C(O)=O.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.[Cl-].[Na+].O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:13]3)=[O:7])=[CH:30][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 221256945-(4-Fluorobenzoyl)-6-trifluoromethylsulfonyloxy-2-methylsulfonylnaphthalene

生成物 1

HCID 154346195-(4-Fluoro-benzoyl)-2-methylsulfonylnaphthalene収率 48.3%

試薬・触媒・溶媒 3

HCID 167845
palladium(II) acetate
触媒
HCID 6228Dimethylformamide溶媒
HCID 57417360Sodium chloride; water溶媒

実験手順

A mixture of 5-(4-fluorobenzoyl)-6-trifluoromethylsulfonyloxy-2-methylsulfonylnaphthalene (0.3 g, 0.63 mmol), [prepared as described in step 1 above], formic acid (0.096 ml, 2.5 mmol), triethylamine(0.36 ml, 2.5 mmol), palladium acetate (14 mg, 0.06 mmol), and 1,3-bis(diphenylphosphino)propane (0.10 g, 0.03 mmol) in DMF (10 ml) was stirred at room temperature. After 16 h, the reaction mixture was poured into brine and extracted into ethyl acetate. The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified by flash chromatography (gradient elution 10-30% ethyl acetate/hexanes) and then recrystallized from ethyl acetate-hexanes to give 0.1 g of 5-(4-fluoro-benzoyl)-2-methylsulfonylnaphthalene as a solid (48% yield).

後処理

  1. extractionextracted into ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography (gradient elution 10-30% ethyl acetate/hexanes)
  6. customrecrystallized from ethyl acetate-hexanes

出典と根拠

ORDレコード
ord-7ab4f2a98c8749629837e8ee7d396d83
出典データセット
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06150397

反応ノート

読み込み中…

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