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

HRID 1185633Notes

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-ac861ef9a83e48f4bb993548d2ec4f60
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669234B2

Reaction notes

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