1-Bromonaphthalene → HCID 58036794, Verbindung

HRID 1028363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1028363
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[C:17]1([P:23]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[C:28]3[C:33]=2[N:32]=[CH:31][CH:30]=[CH:29]3)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH4+].[Cl-]>C1COCC1>[C:34]1([P:23]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[C:28]3[C:33]=2[NH:32][CH:31]([C:2]2[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:5]=[CH:4][CH:3]=2)[CH:30]=[CH:29]3)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Komponenten

6

Edukt 4

HCID 70011-BromonaphthaleneHCID 25517Ammonium ChlorideHCID 6286598-(Diphenylphosphino)quinolineHCID 178418339Butyllithium

Produkt 1

HCID 58036794HCID 58036794, VerbindungAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 1-bromonaphthalene (8.57 mL, 60 mmol) in dry THF (100 mL) under nitrogen was added n-BuLi (37.5 mL, 1.6 M in hexanes, 60 mmol) at −78° C. and the solution was stirred for 30 minutes at −78° C. before adding 8-diphenylphoshinoquinoline (1) (9.4 g, 30 mmol). After stirring at 0° C. for 10 minutes the solution was again cooled down to −78° C., saturated aqueous NH4Cl solution (10 mL) was added and the mixture was warmed to room temperature. Products were then extracted with EtOAc, washed with water and saturated aqueous NaCl, dried (MgSO4) and evaporated to give the 11 as a tan solid (13.0 g, 98%). 1H NMR (400.13 MHz, CDCl3) δ 8.0-7.9 (m, 1H, C5′—H), 7.8-7.7 (m, 1H, C8′—H), 7.66 (d, 1H, J=8.0 Hz, C2′—H), 7.5-7.3 (m, 2H, C6′/7′—H), 7.36 (d, 1H, J=6.4 Hz, C4′—H), 7.3-7.1 (m, 11H, C3′—H/Ph-H), 6.86 (dd, 1H, J=7.2, 1.2 Hz, C5—H), 6.64 (ddd, 1H, J=8.0, 6.4, 1.6 Hz, C7—H), 6.48 (t, 1H, J=7.6 Hz, C6—H), 6.35 (dd, 1H, J=9.6, 1.6 Hz, C4—H), 6.16 (t, 1H, J=1.6 Hz, C2—H), 5.70 (ddd, 1H, J=10.0, 3.6, 1.6 Hz, C3—H), 5.02 (bd, 1H, J=7.6 Hz, N—H) ppm; 13C NMR (100.61 MHz, CDCl3) δ 146.6, 146.5, 139.8, 129.5, 128.7, 128.6, 128.5, 128.4, 128.3 (m), 127.7, 135.1 (d, J=8.1 Hz), 134.9 (d, J=7.1 Hz), 134.5 (d, J=5.1 Hz), 133.9, 133.5 (d, J=13.1 Hz), 133.3 (d, J=12.1 Hz), 126.2, 125.6, 125.3, 125.2, 124.8, 124.4, 122.5, 118.8, 117.1, 116.3, 54.0 ppm; 31P NMR (161.97 MHz, CDCl3) δ −23.1 ppm.

Aufarbeitung

  1. stirringAfter stirring at 0° C. for 10 minutes the solution
  2. additionwas added
  3. temperaturethe mixture was warmed to room temperature
  4. extractionProducts were then extracted with EtOAc
  5. washwashed with water and saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-321887a36f0a4cee974c68c5aef7b669
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735583B2

Notizen zur Reaktion

Wird geladen…