Water → HCID 86708721, compound

HRID 1751384Notes

Reaction equation

[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([Br:16])=[CH:10][CH:11]=3)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[CH2:17]([Sn](CCCC)(CCCC)C(OCC)=C)[CH2:18]CC.BrN1C(=[O:41])CCC1=O.O>O1CCOCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:16][CH2:9][C:10]([C:11]1[CH:18]=[CH:17][C:6]2[C:5]3[C:4](=[CH:3][C:2]([Br:1])=[CH:15][CH:14]=3)[CH2:13][CH2:8][C:7]=2[CH:12]=1)=[O:41]

Participants

Conditions

Temperature: 85 °C

Procedure

A degassed mixture of 2,7-dibromo-9,10-dihydrophenanthrene (3.5 g, 10.35 mmol), tributyl-(1-ethoxyvinyl)tin (3.8 mL, 11.4 mmol), tetrakis(triphenylphosphine)palladium(0) (598 mg, 0.52 mmol) and dichloro[1,1-bis(diphenyl-phosphino)ferrocene]palladium(II) (378 mg, 0.52 mmol) in 1,4-dioxane (1.0 mL) was heated to 85° C. for 18 hours, cooled to room temperature and N-bromosuccinimide (2.21 g, 12.42 mmol) and water (25 mL) were added. The reaction mixture was stirred at room temperature for 2 hours, diluted with ethyl acetate. The organics were washed with water and brine, dried (Na2SO4), and concentrated. The crude residue was purified by flash chromatography to yield 2-bromo-1-(7-bromo-9,10-dihydrophenanthren-2-yl)ethanone (635 mg, 16%).

Workup

temperaturecooled to room temperature
washThe organics were washed with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record: ord-19033b00d8f44dfeb655849ce2140de4
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156823B2

Reaction notes

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