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Supplemental Product Information:
Contents (per one capsule)
Xphos ca. 0.125 mmol
Uses of Reagent
Applicable to palladium-catalyzed reactions due to a ligand encapsulated in HPMC capsules
P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ eye protection/ face protection. P337 + P313 : If eye irritation persists: Get medical advice/ attention. P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P302 + P352 : IF ON SKIN: Wash with plenty of soap and water. P332 + P313 : If skin irritation occurs: Get medical advice/ attention. P362 : Take off contaminated clothing and wash before reuse.
Pd2(dba)3 (HPMC encapsulated) (one capsule) and XPhos (HPMC encapsulated) (one capsule) were added to a solution of 4-bromoanisole (1.21 g, 6.47 mmol), cesium carbonate (6.32 g, 19.4 mmol, 3 eq.) and potassium phenyltrifluoroborate (1.43 g, 7.76 mmol, 1.2 eq.) in THF/water (4:1, 20 mL) at room temperature and the reaction mixture was stirred at 65 °C for 2 hours. The solution was then diluted with ethyl acetate (15 mL) and sat. Na2SO4 aq. (15 mL), and filtered through Celite pad. The filtrate was extracted with ethyl acetate (10 mL x 2) and the organic layer was washed with water (10 mL) and brine (10 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (hexane) to afford 4-methoxybiphenyl (1.09 g, 90% yield) as a white solid.
Experimenter’s Comments
The reaction mixture was monitored by UPLC. The material of the capsule is water-soluble HPMC (hydroxypropyl methylcellulose). The capsule has the shape shown in Fig. 1 and XPhos (ca. 125 μmol) and Pd2(dba)3 (ca. 60 μmol) are encapsulated in each capsule, respectively.
Fig. 1. Appearance of capsule The capsule dissolves in water or polar solvent as shown in Fig. 2. Fig. 2. Capsule disintegrating (left) Immediately after the addition of the capsule, (right) 15 minutes after the addition of the capsule.
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