Hydrochloric Acid → {2-Chloro-4-[(propan-2-yl)oxy]phenyl}boronic acid

HRID 51024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51024
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH:14]([CH3:16])[CH3:15])=[CH:9][C:8]=1[Cl:17].C[O:19][B:20](OC)[O:21]C.Cl>C1COCC1>[Cl:17][C:8]1[CH:9]=[C:10]([O:13][CH:14]([CH3:16])[CH3:15])[CH:11]=[CH:12][C:7]=1[B:20]([OH:21])[OH:19]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 227354041-Bromo-2-chloro-4-isopropoxybenzeneHCID 178418339Butyllithium

Produkt 1

HCID 22735874{2-Chloro-4-[(propan-2-yl)oxy]phenyl}boronic acidAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

n-Butyllithium (1.6 M solution in hexanes, 23.5 mmol, 14.7 mL) was added to 1-bromo-2-chloro-4-iso-propoxybenzene (19.4 mmol, 4.85 g) in THF (120 mL) at −78° C. under an atmosphere of nitrogen. After stirring for thirty minutes the trimethylborate (76.6 mmol, 8.7 mL) was added over twenty minutes. The reaction was allowed to warm to room temperature overnight while stirring. The solution was then acidified with HCl (3 M, 200 mL), and extracted into EtOAc. The EtOAc was then extracted with NaOH (1 N, 4×100 mL), which was subsequently acidified with concentrated HCl forming (2-Chloro-4-iso-propoxyphenyl)boronic acid (1.82 g, 44%) as a white precipitate, which was filtered and dried. 1H NMR (CD3OD, 300 MHz): 7.19 (1H, d, J 8.4 Hz), 6.87 (1H, d, J 2.2 Hz), 6.82 (1H, dd, J 8.4 and 2.2 Hz), 4.58 (1H, m), 1.28 (6H, d, J 5.9 Hz.)

Aufarbeitung

  1. additionwas added over twenty minutes
  2. extractionextracted into EtOAc
  3. extractionThe EtOAc was then extracted with NaOH (1 N, 4×100 mL), which

Quellen und Nachweise

ORD-Eintrag
ord-09b6de8d2b764667a06828ef9d77f6e0
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713471B1

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