5-(Benzyloxy)-2-bromobenzaldehyde → 4-(Benzyloxy)-1-bromo-2-vinylbenzene

HRID 860706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860706
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([Br:23])=[C:19]([CH:22]=1)[CH:20]=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1OCCOCCOCCOCCOCCOC1.C1COCC1>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([Br:23])=[C:19]([CH:20]=[CH2:1])[CH:22]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

6

Edukt 2

HCID 108700245-(Benzyloxy)-2-bromobenzaldehydeHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 692072164-(Benzyloxy)-1-bromo-2-vinylbenzeneAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 2855718-Crown-6KatalysatorHCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyltriphenylphosphonium bromide (12.4 g, 0.0347 mol) and 18-crown-6 (90 mg, 0.41 mmol) were added to THF (100 mL). The mixture was cooled in a ice-water bath. Potassium tert-butoxide (34.7 mL of 1.0M in THF, 0.0347 mol) was added via cannula to the stirred solution. 5-(Benzyloxy)-2-bromobenzaldehyde (9.2 g, 0.0316 mol) was added in one portion which resulted in a slight exotherm. After 30 minutes the cooling bath was removed and stirring was continued at 22° C. for 5 hours. The mixture was concentrated and the residue was purified by flash column chromatography on SiO2 (75 g) with hexanes/ethyl acetate (95:5) to provide 4-(benzyloxy)-1-bromo-2-vinylbenzene as a clear oil (7.9 g, 86% yield). 1H NMR (300 MHz, CDCl3) δ 5.03 (s, 2H), 5.32 (d, J=10.98 Hz, 2H,) 5.63 (d, J=17.20 Hz, 2H), 6.74 (dd, J=8.78, 2.93 Hz, 2H), 6.98 (dd, J=17.57, 10.98 Hz, 2H), 7.13 (d, J=2.93 Hz, 2H), 7.33 (m, 6H).

Aufarbeitung

  1. temperatureThe mixture was cooled in a ice-water bath
  2. customresulted in a slight exotherm
  3. customAfter 30 minutes the cooling bath was removed
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by flash column chromatography on SiO2 (75 g) with hexanes/ethyl acetate (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-14b84c4dfcab448582096ef09318d304
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153848B2

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