Water → 2-Bromo-1-[9-(2-bromo-acetyl)-5,7-dihydro-dibenzo[c,e]oxepin-3-yl]-ethanone

HRID 71705

反応式

[Br:1][C:2]1C=C[C:5]2[C:11]3[CH:12]=[CH:13][C:14](Br)=[CH:15][C:10]=3[CH2:9]O[CH2:7][C:6]=2[CH:17]=1.C([Sn](CCCC)(CCCC)[CH:23]=[CH:24][O:25][CH2:26][CH3:27])CCC.[OH2:36].C1C(=O)N([Br:44])C(=O)C1.[O:45]1[CH2:50][CH2:49]OCC1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][CH2:2][C:17]([C:6]1[CH:5]=[CH:11][C:12]2[C:13]3[CH:14]=[CH:15][C:10]([C:50](=[O:45])[CH2:49][Br:44])=[CH:9][C:23]=3[CH2:24][O:25][CH2:26][C:27]=2[CH:7]=1)=[O:36]

参加物

反応条件

温度: 80 °C

実験手順

To the solution of 3,9-dibromo-5,7-dihydro-dibenzo[c,e]oxepine (416 mg, 1.2 mmol) and tributyl(ethoxyvinyl)stannane (878 μl, 2.6 mmol) in dioxane (6 ml) was added PdCl2(PPh3)2 (30 mg). The mixture was heated at 80° C. for 16 hours and was cooled to 0° C. Water (2 ml) was added, followed by slow addition of NBS (464 mg, 2.6 mmol) over 5 minutes period. The mixture was stirred at 0° C. for additional 40 minutes, and the solvent was removed under reduced pressure. The mixture was diluted with EtOAc, and was washed with water and brine and dried with sodium sulfate. Concentration and purification by flash column chromatography (hexane/EtOAc) gave 2-bromo-1-[9-(2-bromo-acetyl)-5,7-dihydro-dibenzo[c,e]oxepin-3-yl]-ethanone (160 mg).

後処理

temperaturewas cooled to 0° C
customthe solvent was removed under reduced pressure
additionThe mixture was diluted with EtOAc
washwas washed with water and brine
dry with materialdried with sodium sulfate
concentrationConcentration and purification by flash column chromatography (hexane/EtOAc)

出典と根拠

ORDレコード: ord-a27c72c2ed2a44b5af2aeef12d6ead7e
出典データセット: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08822430B2

反応式

参加物

反応物 5

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

関連ノート