Ethyl Acetate → tert-Butyl(1-((2-(bromomethyl)benzyl)oxy)-3-(4-bromophenyl)propan-2-yl)carbamate

HRID 1429364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1429364
[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26]O)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:36])C(=O)C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(=O)OCC>C1COCC1>[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)[CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][Br:36])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 123944090tert-Butyl(1-(4-bromophenyl)-3-((2-(hydroxymethyl)benzyl)oxy)propan-2-yl)carbamate

Produkt 1

HCID 123844053tert-Butyl(1-((2-(bromomethyl)benzyl)oxy)-3-(4-bromophenyl)propan-2-yl)carbamateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of compound 3h (4.15 g, 9.2 mmol) in dry THF (50 mL) was added NBS (4.1 g, 23 mmol) and PPh3 (6 g, 23 mmol) at 0° C. The mixture was stirred at 0° C. for 20 min. Then the mixture was stirred at rt for 2 hr. The solvent was evaporated in vacuo and purified by CC eluting with PE:EA=4:1 to give 3i as a white solid (2.3 g, 50% yield).

Aufarbeitung

  1. stirringThen the mixture was stirred at rt for 2 hr
  2. customThe solvent was evaporated in vacuo
  3. custompurified by CC
  4. washeluting with PE

Quellen und Nachweise

ORD-Eintrag
ord-67bd00b7885d4893a4db9754282a1d4d
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940722B2

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