Phosphorus oxide (P4O10) → 2-(3-Bromo-phenyl)-1-(5-phenyl-furan-2-yl)-ethanone

HRID 1444330

反応式

HRID 1444330 の反応式
[C:1]1([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:12][C:13]1[CH:14]=[C:15]([CH2:19][C:20](O)=[O:21])[CH:16]=[CH:17][CH:18]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>ClC1C=CC=CC=1Cl>[Br:12][C:13]1[CH:14]=[C:15]([CH2:19][C:20]([C:9]2[O:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:11][CH:10]=2)=[O:21])[CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 14812Phosphorus oxide (P4O10)2 回HCID 74653(3-Bromophenyl)acetic acidHCID 5193632-Phenylfuran

生成物 1

HCID 596547282-(3-Bromo-phenyl)-1-(5-phenyl-furan-2-yl)-ethanone

試薬・触媒・溶媒 1

HCID 72391,2-Dichlorobenzene溶媒2 回

反応条件

温度
80 °C

実験手順

2-Phenyl-furan (119) (50 mg, 0.28 mmol) and (3-bromo-phenyl)-acetic acid (134 mg, 0.63 mmol) were dissolved in ortho-dichlorobenzene (4 ml). P2O5 (202 mg, 1.42 mmol) was added as a suspension in ortho-dichlorobenzene (2 ml). The reaction mixture was heated to 80° C. for 2 h and cooled to room temperature overnight. After the addition of further P2O5 (202 mg, 1.42 mmol), heating was resumed at 90° C. for 3 h. The reaction mixture was cooled to 0° C. and quenched with H2O (15 ml). The organic layer was separated and the aqueous layer was washed with DCM (3×10 ml). The combined organic layers were dried (MgSO4), filtered and the DCM removed in vacuo. The ortho-dichlorobenzene solution was loaded to a silica-gel column and flushed with heptane (100 ml). The title compound was then eluted with 10% EtOAc in heptane.

後処理

  1. temperaturecooled to room temperature overnight
  2. temperatureheating
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. customquenched with H2O (15 ml)
  5. customThe organic layer was separated
  6. washthe aqueous layer was washed with DCM (3×10 ml)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. customthe DCM removed in vacuo
  10. customflushed with heptane (100 ml)
  11. washThe title compound was then eluted with 10% EtOAc in heptane

出典と根拠

ORDレコード
ord-c3b5924588204046aff485ab80bd94be
出典データセット
uspto-grants-2010_02
特許番号
US07662839B2

関連ノート

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