Toluene → HCID 86682765, compound

HRID 1481947Notes

Reaction equation

FC(F)(F)S(O)(=O)=O.[CH:9]1[C:23]2=[C:24]3[C:16]([C:17]4[C:22]2=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:15][CH:14]=[CH:13][C:12]3=[C:11]([C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[CH:31]=[CH:30][CH:29]=[CH:28]3)[CH:10]=1.B(O)O.[CH2:38](COC)OC.C([O-])([O-])=O.[Na+].[Na+].[C:50]1([CH3:56])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>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>[CH:56]([C:50]1[CH:55]=[CH:54][C:53]([C:30]2[CH:31]=[C:32]3[C:27](=[CH:28][CH:29]=2)[CH:26]=[C:25]([C:11]2[CH:10]=[CH:9][C:23]4[C:22]5[C:17]([C:16]6[C:24]=4[C:12]=2[CH:13]=[CH:14][CH:15]=6)=[CH:18][CH:19]=[CH:20][CH:21]=5)[CH:34]=[CH:33]3)=[CH:52][CH:51]=1)=[CH2:38]

Participants

Conditions

Temperature: 85 °C

Procedure

6-(fluoranthene-3-yl)naphthalene trifluoromethane sulfonate (0.16 g, 0.33 mmol), boronic acid (0.054 g, 0.36 mmol) and Pd(PPh3)4 (0.194 g, 0.17 mmol) were placed in a 2-neck RB flask and placed under nitrogen atmosphere. Toluene (25 mL) and Dimethoxyethane (25 mL) was then added to the reaction mixture followed by aq. Na2CO3 (2 M, 1.0 ml). The reaction mixture was refluxed at 85° C. for 24 h and diluted with Toluene and filtered through a celite bed. The combined organic extracts was evaporated to dryness and purified by silica column chromatography using dichloromethane and pet-ether (40-60° C.) to give slightly yellow coloured powder the product (0.05 g).

Workup

filtrationfiltered through a celite bed
customThe combined organic extracts was evaporated to dryness
custompurified by silica column chromatography
customdichloromethane and pet-ether (40-60° C.)

Sources & evidence

ORD record: ord-613f1ed54dfa489db044e462505bbb36
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09410080B2

Reaction notes

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