반응 #1184126

ord-8e9dcc039968418fba609e68a6da4c6f

반응 방정식

COC(=O)c1ccc(Br)cc1
methyl 4-bromobenzoate
OB(O)c1cc2ccccc2s1
2-benzo[b]thiopheneboronic acid
O=C([O-])[O-].[K+].[K+]
potassium carbonate
COC(=O)c1ccc(-c2cc3ccccc3s2)cc1
title compound
COC(=O)c1ccc(-c2cc3ccccc3s2)cc1
Methyl 4-(benzo[b]thiophen-2-yl)benzoate

반응 조건

온도
70°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    추출extracted with ethyl acetate
  2. 2
    세척The organic layer was washed with aqueous saturated sodium chloride solution
  3. 3
    건조dried with sodium sulfate
  4. 4
    농축concentrated under reduced pressure
  5. 5
    기타The residue was purified through silica gel column chromatography

실험 절차

A mixture of methyl 4-bromobenzoate (430 mg, 2.00 mmol), 2-benzo[b]thiopheneboronic acid (392 mg, 2.20 mmol), palladium(0) acetate (2.2 mg, 0.010 mmol), potassium carbonate (691 mg, 5.00 mmol), tetrabutylammonium bromide (645 mg, 2.00 mmol) and water (2.2 mL) was stirred in a nitrogen atmosphere at 70° C. for 1 hour. Water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried with sodium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography to obtain the title compound as a pale yellow solid.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08138197B2uspto-grants-2012_03