4-Methoxybenzyl alcohol → 4-Methoxybenzyl 2-bromoacetate

HRID 1378717

Reaktionsgleichung

Reaktionsgleichung von HRID 1378717
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][OH:10])=[CH:7][CH:8]=1.C(N(CC)CC)C.[Br:18][CH2:19][C:20](Br)=[O:21]>C(Cl)Cl>[Br:18][CH2:19][C:20]([O:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:21]

Komponenten

5

Edukt 3

HCID 77384-Methoxybenzyl alcoholHCID 8471TriethylamineHCID 61147Bromoacetyl bromide

Produkt 1

HCID 132332344-Methoxybenzyl 2-bromoacetateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a -78 ° C. solution of p-methoxybenzyl alcohol (6.91 g, 50 mmol) and triethylamine (6.95 mL, 50 mmol) in anhydrous CH2Cl2 (50 mL) was added a solution of bromoacetyl bromide (10.1 g, 50 mmol) in CH2Cl2 at -78° C. under nitrogen, over a period of 10 min. The cooling bath was removed, and the reaction mixture was stirred for 2 h. The mixture was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated to provide 12 g (93% yield) of p-methoxybenzyl bromoacetate as a dark colored oil which was used in the next reaction without purification. A portion was purified by column chromatography on silica gel (elution with 20% ethyl acetate/hexanes) to give a clear, colorless oil. 1H NMR (300 MHz, CDCl3 ) δ3.79 (s, 3 H), 3.83 (s, 2 H), 5.12 (s, 2 H), 6.87 (m, 2 H), and 7.30 (m, 2 H); IR (film) 1738 cm-1 ; MS (ESI/NH4OAc) M+NH4+ =276.

Aufarbeitung

  1. customThe cooling bath was removed
  2. washThe mixture was washed with water and saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e54384815ce947099ae8325f54cc7bb8
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668290

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