Bromine → Ethyl 2-(4-methoxybenzyloxy)-2-(4-bromo-1-hydroxy-3-methylnaphthalen-2-yl)acetate

HRID 514120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 514120
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][O:8][CH:9]([C:15]2[C:24]([CH3:25])=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[OH:26])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+].[Br:34]Br.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][CH:9]([C:15]2[C:24]([CH3:25])=[C:23]([Br:34])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[OH:26])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:27][CH:28]=1

Komponenten

6

Edukt 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 67126181Ethyl 2-(4-methoxybenzyloxy)-2-(1-hydroxy-3-methylnaphthalen-2-yl)acetate

Produkt 1

HCID 67126193Ethyl 2-(4-methoxybenzyloxy)-2-(4-bromo-1-hydroxy-3-methylnaphthalen-2-yl)acetateAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

A solution of ethyl 2-(4-methoxybenzyloxy)-2-(1-hydroxy-3-methylnaphthalen-2-yl)acetate (102 mg, 0.268 mmol) in CHCl3 (5.0 mL) was treated with solid NaHCO3 (46 mg, 0.281 mmol). Br2 (45 mg) in CHCl3 (1.0 mL) was added dropwise over 5 min at 23° C. After 15 min, 10% Na2S2O3 (10 mL) was added. The reaction was extracted two times with CHCl3. Combined organic phases were dried (Na2SO4), filtered, and concentrated. The residue was dissolved in DCM. The solution was wet-loaded onto a 12 g “gold” ISCO silica gel column and purified by flash chromatography (ethyl acetate/hexanes) giving the desired product (83 mg, 67%). 1H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 8.29 (d, J=8.2 Hz, 1H), 8.22 (d, J=8.6 Hz, 1H), 7.59 (dd, J=7.4, 7.4 Hz, 1H), 7.47 (dd, J=7.8, 7.8 Hz, 1H), 7.26 (d, J=8.2 Hz, 2H), 6.91 (d, J=8.6 Hz, 2H), 5.47 (s, 1H), 4.67-4.56 (m, 2H), 4.26-4.08 (m, 2H), 3.81 (s, 3H), 2.60 (s, 3H), 1.20 (t, J=7.1 Hz, 3H).

Aufarbeitung

  1. extractionThe reaction was extracted two times with CHCl3
  2. dry with materialCombined organic phases were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in DCM
  6. custompurified by flash chromatography (ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c5d509d3e921468ca9bfe6d46ed86d47
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102614B2

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