1-Bromo-4-((methylsulfonyl)methyl)benzene → 4,4,5,5-Tetramethyl-2-(4'-((methylsulfonyl)methyl)-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane

HRID 1050237

Reaktionsgleichung

Reaktionsgleichung von HRID 1050237
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[CH3:13][C:14]1([CH3:36])[C:18]([CH3:20])([CH3:19])[O:17][B:16]([C:21]2[CH:26]=[CH:25][C:24](B3OC(C)(C)C(C)(C)O3)=[CH:23][CH:22]=2)[O:15]1>C1COCC1.C(=O)([O-])[O-].[Ag+2].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>[CH3:19][C:18]1([CH3:20])[C:14]([CH3:13])([CH3:36])[O:15][B:16]([C:21]2[CH:26]=[CH:25][C:24]([C:2]3[CH:7]=[CH:6][C:5]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=3)=[CH:23][CH:22]=2)[O:17]1

Komponenten

6

Edukt 2

HCID 27614151-Bromo-4-((methylsulfonyl)methyl)benzeneHCID 105924952,2'-(1,4-Phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Produkt 1

HCID 900593934,4,5,5-Tetramethyl-2-(4'-((methylsulfonyl)methyl)-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 178418647HCID 178418647, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1-bromo-4-((methylsulfonyl)methyl)benzene (1.5 g, 6.02 mmol), 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (4.97 g, 15.05 mmol), and silver carbonate (1.826 g, 6.62 mmol) were dissolved in THF (60.2 ml) and sparged with N2 for 15 min. Then Pd(PPh3)4 (0.348 g, 0.301 mmol) was added and the reaction was heated to 80° C. overnight. The reaction was then cooled to rt, filtered through Celite™ and concentrated in vacuo. The resulting residue was purified by column chromatography on a Biotage™ 50 g column by eluting with 5% to 50% EtOAc:Hex to yield the desired product. 1H NMR δ (ppm) 7.83 (d, 2H), 7.69 (d, 2H), 7.64 (d, 2H), 7.54 (d, 2H), 4.46 (s, 2H), 2.89 (s, 3H), 1.4 (12H).

Aufarbeitung

  1. customsparged with N2 for 15 min
  2. temperatureThe reaction was then cooled to rt
  3. filtrationfiltered through Celite™
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography on a Biotage™ 50 g column
  6. washby eluting with 5% to 50% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-3ca29cbe1875486984f01544e6e6fc8e
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382243B2

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