Boron tribromide → 1-formyl-2,3-dihydro-1H-indene-4-carbonitrile

HRID 2173243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173243
C[O:2]/[CH:3]=[C:4]1\[CH2:5][CH2:6][C:7]2[C:8]([C:13]#[N:14])=[CH:9][CH:10]=[CH:11][C:12]\1=2.B(Br)(Br)Br>C(Cl)Cl>[CH:3]([CH:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:13]#[N:14])[C:7]=2[CH2:6][CH2:5]1)=[O:2]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 68431673(1E)-1-[(methyloxy)methylidene]-2,3-dihydro-1H-indene-4-carbonitrile

Produkt 1

HCID 595686981-formyl-2,3-dihydro-1H-indene-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (1E)-1-[(methyloxy)methylidene]-2,3-dihydro-1H-indene-4-carbonitrile (250 mg, 1.05 mmol) in DCM (5 mL) was added BBr3 dropwise at −78° C. under N2. Then the mixture was stirred at this temperature for 3 h. It was poured into ice-saturated NaHCO3 solution, and extracted with DCM. The organic layer was washed with brine and dried over Na2SO4. The solvent was removed in vacuo to give crude 1-formyl-2,3-dihydro-1H-indene-4-carbonitrile, which is used for next step directly. 1H-NMR (400 MHz, CDCl3) δ ppm 9.72 (s, 1H), 7.54 (d, J=7.6 Hz, 2H), 7.34 (t, J=7.6 Hz, 1H), 3.76 (s, 1H), 3.18-3.24 (m, 2H), 2.42-2.58 (m, 2H).

Aufarbeitung

  1. additionIt was poured into ice-saturated NaHCO3 solution
  2. extractionextracted with DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6a79dc60a63c4fa8a86bfe22faec0874
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056859B2

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