P-Xylene → 5-(Tert-butyl-dimethyl-silanyloxy)-2-[4-(tert-butyl-dimethyl-silanyloxy)-3-fluoro-phenyl]-7-vinyl-benzooxazole

HRID 1247211Notes

Reaction equation

Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[C:13]([F:25])[CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH:3]=1.[CH2:34]([Sn](CCCC)(CCCC)C=C)[CH2:35]CC.CC1C=CC(C)=CC=1>C(OCC)C.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[Si:27]([O:26][C:4]1[CH:3]=[C:2]([CH:34]=[CH2:35])[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[C:13]([F:25])[CH:12]=3)=[N:7][C:6]=2[CH:5]=1)([C:30]([CH3:33])([CH3:31])[CH3:32])([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 90 °C

Procedure

Dichlorobis(tri-o-tolylphosphine)palladium (II) (0.63 g, 0.79 mmol) was added into a mixture of 7-bromo-5-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-{[tert-butyl(dimethyl)silyl]oxy}-3-fluorophenyl)-1,3-benzoxazole (14.7 g, 26.6 mmol), tributyl(vinyl)tin. (10.5 g, 33.25 mmol) and p-xylene (85 mL). The reaction mixture was stirred at 90° C. for 24 h, cooled to room temperature, diluted with ethyl ether (100 mL) and treated with activated carbon. The mixture was filtered through MgSO4 and concentrated. Purification by flash chromatography (hexanes/EtOAc 50/1) gave a white solid (11.8 g, 89% yield, m.p. 93–95° C.); MS m/e 500 (M+H)+.

Workup

temperaturecooled to room temperature
additiontreated with activated carbon
filtrationThe mixture was filtered through MgSO4
concentrationconcentrated
customPurification by flash chromatography (hexanes/EtOAc 50/1)

Sources & evidence

ORD record: ord-76710e5c3540451c9f1d0aa144be507e
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129258B2

Reaction notes

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