Pyridine → 3,5-Dichloro-4-(4-methoxyphenoxy)benzyl Alcohol

HRID 1063873

Reaktionsgleichung

Reaktionsgleichung von HRID 1063873
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[Cl:12][C:13]1[CH:18]=[C:17]([CH2:19][OH:20])[CH:16]=[C:15]([Cl:21])[C:14]=1[OH:22].N1C=CC=CC=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[Cl:12][C:13]1[CH:18]=[C:17]([CH:16]=[C:15]([Cl:21])[C:14]=1[O:22][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:19][OH:20]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 8471TriethylamineHCID 176409Benzenemethanol, 3,5-dichloro-4-hydroxy-HCID 201262(4-Methoxyphenyl)boronic acid

Produkt 1

HCID 222856543,5-Dichloro-4-(4-methoxyphenoxy)benzyl AlcoholAusbeute 44,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a flask containing 24 ml of dichloromethane was added 4 A sieves (2.97 g, activated at 500° C. for 8 h), 4-methoxyphenylboronic acid (1.84 g, 12.0 mmol), 2,6-dichloro-4-hydroxymethylphenol (465 mg, 2.41 mmol), copper (II) acetate (438 mg, 2.41 mmol), pyridine (0.97 ml, 12.0 mmol) and triethylamine (1.67 ml, 12.0 mmol). The reaction flask was fitted with a drying tube and stirred overnight. Filtration through celite and removal of volatiles in vacuo followed by column chromatography (silica, 30% ethyl acetate in hexane) provided the title compound as light brown oil (323 mg, 44%). 1H NMR (400 MHz, CDCl3) δ 7.39 (s, 2H), 6.82 (d, j=7.2 Hz, 2H), 6.77 (d, j=7.2 Hz, 2H), 4.69 (s, 2H), 3.76 (s, 3H).

Aufarbeitung

  1. customThe reaction flask was fitted with a drying tube
  2. filtrationFiltration
  3. customthrough celite and removal of volatiles in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8bdd5a8db7ac4a48952c388ce2db5398
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06967220B2

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