Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Triethylamine → Methyl 3-nitro-5-[(trimethylsilyl)ethynyl]benzoate
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Triethylamine | HCID 8471 | — |
| 반응물 | Trimethylsilylacetylene | HCID 66111 | — |
| 반응물 | Methyl 3-bromo-5-nitrobenzoate | HCID 239341 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 촉매 | HCID 178418476 | HCID 178418476 | — |
| 용매 | Hydrochloric Acid | HCID 313 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 생성물 | Methyl 3-nitro-5-[(trimethylsilyl)ethynyl]benzoate | HCID 57961569 | 88% |
반응 단계
A solution of methyl 3-bromo-5-nitrobenzoate (0.331 g, 1.27 mmol), (trimethylsilyl)acetylene (0.27 mL, 1.9 mmol), bis(triphenylphosphine)palladium(II) chloride (45 mg, 0.064 mmol), copper(I) iodide (19 mg, 0.10 mmol) and triethylamine (0.26 mL, 1.9 mol) in DMF (5 mL) was stirred at room temperature overnight. The solution was diluted with ethyl acetate and 1 N HCl. The aqueous layer was extracted with ethyl acetate once, and the combined organic solutions were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography (10% ethyl acetate in hexanes) to give the desired product (310 mg, 88%). LCMS for C13H16NO4Si (M+H)+: m/z=278.1.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US08871753B2 |
| 출처 데이터셋 | uspto-grants-2014_10 |
| ORD ID | ord-67d343bf7e1b4022b90e0219bb2f0e9a |
| 출처 메모 | uspto-grants-2014_10 |