تفاعل #1842134

ord-d75bce3794684856ad7adbdcfcaffb21

معادلة التفاعل

C[Si](C)(C)C=[N+]=[N-]
(Trimethylsilyl)diazomethane
Cc1cc(C(=O)O)c(F)cc1Br
4-bromo-2-fluoro-5-methyl-benzoic acid
CO
MeOH
COC(=O)c1cc(C)c(Br)cc1F
methyl 4-bromo-2-fluoro-5-methyl-benzoate
المردود 82.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    تركيزconcentrated under reduced pressure
  2. 2
    أخرىThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=40/1)

الإجراء التجريبي

(Trimethylsilyl)diazomethane (4.0 ml, 8.0 mmol, 2 M in Et2O) was added dropwise to a solution of 4-bromo-2-fluoro-5-methyl-benzoic acid (1.88 g, 8.05 mmol) in benzene (7.5 ml)-MeOH (5.6 ml) at 10±2° C. over 10 minutes. The mixture was stirred at room temperature for 30 minutes and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=40/1) to give methyl 4-bromo-2-fluoro-5-methyl-benzoate (1.62 g, 82%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09169254B2uspto-grants-2015_10