Triethylamine → 2,2,2-Trifluoro-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)ethanol

HRID 723056

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8](=[O:13])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][CH:7]=1.[CH3:14][C:15]1([CH3:22])[C:19]([CH3:21])([CH3:20])[O:18][BH:17][O:16]1.CCN(CC)CC>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>[F:10][C:9]([F:12])([F:11])[CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([B:17]2[O:18][C:19]([CH3:21])([CH3:20])[C:15]([CH3:22])([CH3:14])[O:16]2)[CH:3]=1)[OH:13]

Participants

Conditions

Temperature: 95 °C

Procedure

To an oven-dried round bottom flask fitted with a stir bar and a rubber septum was added 1-(3-bromo-phenyl)-2,2,2-trifluoro-ethanone (560 mg, 2.2 mmol, as prepared in Example 28, step a), 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (0.96 mL, 6.6 mmol, Aldrich Chemical Company), (PPh3)2PdCl2 (93 mg, 0.132 mmol, Strem Chemicals, Inc., Newburyport, Mass.), and Et3N (1.8 mL, 13.2 mmol). The reaction mixture was evacuated, purged with argon, and then suspended in dioxane (16 mL). After stirring for 18 hr at 95° C., the reaction was allowed to cool and then filtered through Celite.® The filtrate was concentrated in vacuo and the residue was purified by chromatography (SiO2, flash elution: 5% EtOAc in hexanes) to give 350 mg (53%) of an oil that was used without further purification.

Workup

customTo an oven-dried round bottom flask fitted with a stir bar
customThe reaction mixture was evacuated
custompurged with argon
temperatureto cool
filtrationfiltered through Celite
concentration® The filtrate was concentrated in vacuo
customthe residue was purified by chromatography (SiO2, flash elution: 5% EtOAc in hexanes)

Sources & evidence

ORD record: ord-6f20438fc21b46779c5e61664dad14d2
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138530B2

Linked notes

Loading…