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

HRID 417414Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

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)

Sources & evidence

ORD record: ord-6c8fc564012c4ec9862136c6435cf5ef
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088368B2

Reaction notes

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