Boron tribromide → 5-Formyl-2-hydroxybenzamide

HRID 841046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 841046
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12]C)[CH:7]=[O:8])(=[O:3])[NH2:2].B(Br)(Br)Br>C(Cl)Cl>[CH:7]([C:6]1[CH:9]=[CH:10][C:11]([OH:12])=[C:4]([CH:5]=1)[C:1]([NH2:2])=[O:3])=[O:8]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 106789093-Carbamoyl-4-methoxy-benzaldehyde2×

Produkt 1

HCID 106545925-Formyl-2-hydroxybenzamideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

3-Carbamoyl-4-methoxy-benzaldehyde compound 41 (1.065 g, 5.95 mmol) was stirred in dry CH2Cl2 (120 mL) at −78° C. under argon. Boron tribromide (10.71 mL, 1.0 M, 10.71 mmol) was added, and the reaction stirred 18 h while warming to 23° C. The reaction was quenched with 0.05 N HCl (80 mL), and was allowed to stir for 15 min. The organic layer was collected, and the aqueous layer was further extracted with EtOAc (2×50 mL). Organics were combined, dried (Na2SO4), and concentrated. Purification by flash chromatography (60% EtOAc/CHCl3) gave 540 mg (55%) of 5-formyl-2-hydroxy-benzamide 42 as a white solid. 1H NMR (DMSO-d6) δ 14.00 (1 H, s), 9.88 (1 H, s), 8.73 (1 H, br s), 8.55 (1 H, d, J=1.5 Hz), 8.21 (1 H, br s), 8.00 (1 H, dd, J=8.7, 1.5 Hz), 7.13 (1 H, d, J=8.7 Hz); IR (KBr) 3420, 3237, 1686, 1618, 1493, 1375, 1279, 1196 cm−1. Anal. (C8H7NO3) C, H, N.

Aufarbeitung

  1. customThe reaction was quenched with 0.05 N HCl (80 mL)
  2. stirringto stir for 15 min
  3. customThe organic layer was collected
  4. extractionthe aqueous layer was further extracted with EtOAc (2×50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by flash chromatography (60% EtOAc/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-e71cfd1d6360430c8e3932e88e8e7b8e
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06369226B1

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