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

HRID 1717112

반응식

HRID 1717112 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 72391,2-Dichlorobenzene용매2회

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f599f61ea1d74a759833779e2948a237
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803841B2

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