تفاعل #2045044

ord-e1fdf190586b47d2bdae6094ee54b428

معادلة التفاعل

COC(=O)COCCBr
(2-bromoethoxy)acetic acid methyl ester
O=[N+]([O-])c1ccc(O)cc1
4-nitrophenol
O=C([O-])[O-].[K+].[K+]
K2CO3
[I-].[Na+]
sodium iodide
COC(=O)COCCOc1ccc([N+](=O)[O-])cc1
59
المردود 43.6%
COC(=O)COCCOc1ccc([N+](=O)[O-])cc1
[2-(4-Nitrophenoxy)ethoxy]acetic acid methyl ester
المردود 43.6%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةrefluxed for 24 hours
  2. 2
    workup.DISTILLATIONAcetone was distilled off
  3. 3
    workup.ADDITIONwater (100 ml) was added
  4. 4
    ترشيحCrude 59 was filtered
  5. 5
    أخرىdried
  6. 6
    أخرىpurified by column chromatography on silica gel

الإجراء التجريبي

To a mixture of 4-nitrophenol (5 g, 36 mmol), anhydrous K2CO3 (20 g, 145 mmol) and sodium iodide (2 grams, 13.3 mmol) in anhydrous acetone (100 ml) was added (2-bromoethoxy)acetic acid methyl ester (11 g, 56 mmol) and refluxed for 24 hours. Acetone was distilled off and water (100 ml) was added. Crude 59 was filtered, dried and purified by column chromatography on silica gel using benzene as eluant to give pure 59 (4 g, 43.6%) as a white fluffy powder. M.p: 96-97.8° C.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08409559B2uspto-grants-2013_04