Dichloromethane → 2-(3-Bromo-phenyl)-1-(5-phenyl-furan-2-yl)-ethanone

HRID 659106

反応式

HRID 659106 の反応式
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:15]1([C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Br:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34](O)=[O:35])[CH:30]=[CH:31][CH:32]=1.C(Cl)Cl>ClC1C=CC=CC=1Cl>[Br:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34]([C:23]2[O:22][C:21]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:25][CH:24]=2)=[O:35])[CH:30]=[CH:31][CH:32]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 14812Phosphorus oxide (P4O10)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

反応条件

温度
80 °C

実験手順

Phosphorous pentoxide (2.02 g, 14.20 mmol) suspended in 1,2-dichlorobenzene (60 mL) was added to a mixture of 2-phenyl-furan (23) (500 mg, 2.84 mmol) and 3-bromophenylacetic acid (24) (1.34 g, 6.25 mmol). The reaction mixture was heated to 80° C. for 2 hours and then cooled to ambient temperature. DCM was added, the organic layer washed with water and partially reduced in vacuo. The crude product was purified by Flash Master Jones Chromatography using a 50 g silica cartridge and first eluting with heptane to remove excess 1,2-dichlorobenzene, then 5-10% EtOAc in heptane to give the title compound. Yield: 278 mg, 38%; LC-MS tr 1.73 min; HPLC Purity: 100%; MS (ES+) m/z 341, 343 (M+H)

後処理

  1. temperaturecooled to ambient temperature
  2. washthe organic layer washed with water
  3. customThe crude product was purified by Flash Master Jones Chromatography
  4. washfirst eluting with heptane
  5. customto remove excess 1,2-dichlorobenzene

出典と根拠

ORDレコード
ord-16232f9a991840aa9087cb202a425d26
出典データセット
uspto-grants-2011_12
特許番号
US08080567B2

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