Reaktionsgleichung
C([Mg]Cl)(C)C.Br[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[C:8]=1[S:15][CH3:16].C[O:18][B:19](OC)[O:20]C>O1CCCC1>[F:14][C:9]1[C:8]([S:15][CH3:16])=[C:7]([B:19]([OH:20])[OH:18])[CH:12]=[C:11]([F:13])[CH:10]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 40 °C
Versuchsvorschrift
Charge a flask with isopropyl magnesium chloride (145 mL, 2M in THF, 290 mmol) and dilute with tetrahydrofuran (150 mL) and heat to 40° C. under nitrogen. Add 1-bromo-3,5-difluoro-2-methylsulfanyl-benzene (28 g, 117 mmol) slowly over 5 minutes. After 30 minutes, cool the reaction to 0° C. and add trimethylborate (46 mL, 410 mmol) diluted with tetrahydrofuran (100 mL) via an addition funnel over 5 minutes. Partition the resulting gelatinous mixture between methylene chloride and 1N HCl. Acidify the aqueous layer to pH˜1 (if needed) and vigorously stir the biphasic mixture until all solids are dissolved. Separate the organic layer. Dry over sodium sulfate, filter and concentrate. Triturate with hexanes and filter to yield 14.7 g (61%) of the title compound.
Aufarbeitung
- temperaturecool
- customthe reaction to 0° C.
- customPartition the resulting gelatinous mixture between methylene chloride and 1N HCl
- dissolutionare dissolved
- customSeparate the organic layer
- dry with materialDry over sodium sulfate
- filtrationfilter
- concentrationconcentrate
- customTriturate with hexanes
- filtrationfilter
Quellen und Nachweise
- ORD-Eintrag
- ord-5b5f1cd02b7f40bcac7180954cd8d843
- Quelldatensatz
- uspto-grants-2012_07
- Patentnummer
- US08217032B2
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