Hydrochloric Acid → 2,3-Dihydro-4-iodo-5-phenylbenzofuran

HRID 617410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 617410
[C:1]1([C:7]2[C:15](N)=[C:11]3[CH2:12][CH2:13][O:14][C:10]3=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.N([O-])=O.[Na+].[I-:22].[K+]>O.[Cl-].[Na+].O.CCOCC>[I:22][C:15]1[C:11]2[CH2:12][CH2:13][O:14][C:10]=2[CH:9]=[CH:8][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 218521822,3-Dihydro-5-phenyl-4-benzofuranamineHCID 23668193Sodium Nitrite

Produkt 1

HCID 218521872,3-Dihydro-4-iodo-5-phenylbenzofuranAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A mechanically stirred solution of 2,3-dihydro-5-phenyl-4-benzofuranamine (1.88 g, 8.90 mmol), ice (~5 g), and concentrated hydrochloric acid (3.9 mL) at 5° C. was treated slowly with a solution of sodium nitrite (0.675 g, 9.78 mmol) in H2O (4 mL). The resulting suspension was stirred 15 min and filtered through a plug of glass wool into a solution of potassium iodide (5.00 g, 30.1 mmol) in H2O. The suspension was allowed to stand for 12 h, treated with Et2O (200 mL) and brine (200 mL), the layers separated, and the aqueous layer further extracted with fresh Et2O (2×300 mL). The combined organic portions were, filtered, washed with 1 N HCl (2×300 mL), brine (200 mL), dried (K2CO3), filtered, and concentrated in vacuo to afford 1.63 g (57%) of the product as a clear oil: 1H NMR (300 MHz, CDCl3) δ 3.23 (t, J=8 Hz, 2H), 4.63 (t, J=8 Hz, 2H), 6.75 (d, J=8 Hz, 1H), 7.02 (d, J=8 Hz, 1H), 7.29-7.42 (m, 5H).

Aufarbeitung

  1. waitto stand for 12 h
  2. customthe layers separated
  3. extractionthe aqueous layer further extracted with fresh Et2O (2×300 mL)
  4. filtrationfiltered
  5. washwashed with 1 N HCl (2×300 mL), brine (200 mL)
  6. dry with materialdried (K2CO3)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0762687139e442a1a0b5dfefb19dd8c3
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05948817

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