Water → 4'-Hydroxy-3-methyl-1,1'-biphenyl-4-carbonitrile

HRID 494850

Reaktionsgleichung

Reaktionsgleichung von HRID 494850
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[C:11]([CH3:17])[CH:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[C:11]([CH3:17])[CH:10]=2)=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 962Water2×HCID 25134Boron tribromideHCID 112183464'-Methoxy-3-methyl-1,1'-biphenyl-4-carbonitrile

Produkt 1

HCID 136359914'-Hydroxy-3-methyl-1,1'-biphenyl-4-carbonitrileAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The product from Example 106A (5.60 g, 25.4 mmol) in CH2Cl2 (120 mL) at 78° C. was treated with 1.0 M BBr3 (in CH2Cl2, 76 mL, 76.0 mmol) dropwise over 1 hour. After stirring for 14 hours at room temperature, the mixture was warmed to 0° C. (ice bath) and treated with water (0.5 mL). After 10 minutes, additional water was added (2.0 mL), ice bath was removed, and 5.0 mL of water was added. The mixture was then treated with another 20 mL of water and allowed to stir for 45 minutes. The mixture was filtered and the filtrate extracted with CH2Cl2. The CH2Cl2 layers were combined, dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure to provide the title compound as an off-white powder (5.04 g, 94% yield). 1HNMR (300 MHz, CDCl3) δ 2.35 (s, 3H), 5.0 (s, 1H), 6.79-7.50 (m, 7H); MS (DCI) m/z 210 (+H)+.

Aufarbeitung

  1. temperaturethe mixture was warmed to 0° C. (ice bath)
  2. waitAfter 10 minutes
  3. customwas removed
  4. addition5.0 mL of water was added
  5. additionThe mixture was then treated with another 20 mL of water
  6. stirringto stir for 45 minutes
  7. filtrationThe mixture was filtered
  8. extractionthe filtrate extracted with CH2Cl2
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationthe filtrate concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bd88652c3e4d49dfbbfe42c5316495bd
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538138B2

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