Triethylamine → 1-(Chloromethyl)-3-fluoro-2-methoxybenzene

HRID 449833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449833
[F:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([CH2:8]O)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.CS([Cl:23])(=O)=O>ClCCl.C(OCC)C>[Cl:23][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[O:10][CH3:11]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22505951(3-Fluoro-2-methoxyphenyl)methanol

Produkt 1

HCID 225059631-(Chloromethyl)-3-fluoro-2-methoxybenzeneAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (3-fluoro-2-methoxyphenyl)methanol (3.02 g, 19.3 mmol) and triethylamine (6.74 mL, 48.4 mmol) in dichloromethane (20 mL) is treated with methanesulfonyl chloride (2.99 mL, 38.7 mmol) slowly at room temperature and stirred under nitrogen for 3 h. The reaction is the diluted with diethyl ether, washed with 0.5 M hydrochloric acid twice, dried over anhydrous sodium sulfate, filtered, and concentrated to afford the title compound as a yellow oil (2.71 g, 80%). 1H NMR (400 MHz, CDCl3) δ 7.15-6.93 (m, 3H), 4.61 (s, 2H), 4.00 (s, 3H).

Aufarbeitung

  1. washwashed with 0.5 M hydrochloric acid twice
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7f0798e1468342ad826ef0fb340b4878
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486943B2

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