Carbon tetrabromide → [4-(3-Bromo-propyl)-phenoxy]-acetic acid methyl ester

HRID 882935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882935
[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14]O)=[CH:8][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:37]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][Br:37])=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22949949Methyl [4-(3-hydroxypropyl)phenoxy]acetate

Produkt 1

HCID 67028183[4-(3-Bromo-propyl)-phenoxy]-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of [4-(3-Hydroxy-propyl)-phenoxy]-acetic acid methyl ester (2.45 g, 10.9 mmol) in DCM (60 mL) is added polymer-supported triphenylphosphine (7.26 g, 21.8 mmol) and carbon tetrabromide (3.47 g, 11.99 mmol) and the resulting reaction mixture is stirred at RT for 15 h. The reaction mixture is filtered to remove the polymer-supported reagent, and then concentrated in vacuo. The residue is purified by chromatography (SiO2, EtOAc:iso-hexane, 1:5) to yield the title compound. 1H NMR (400 MHz, CDCl3) δ 7.14 (2H, d), 6.86 (2H, d), 4.69 (2H, s), 3.83 (3H, s), 3.40 (2H, t), 2.74 (2H, t), 2.15 (2H, m).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture is filtered
  3. customto remove the polymer-supported reagent
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography (SiO2, EtOAc:iso-hexane, 1:5)

Quellen und Nachweise

ORD-Eintrag
ord-d129e1243ed9433980bb5e835b7f8e26
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236808B2

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