참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Water | HCID 962 | — |
| 반응물 | Triethylamine | HCID 8471 | — |
| 반응물 | Benzene, 1-bromo-3-iodo- | HCID 11561 | — |
| 반응물 | 3-Butyn-1-OL | HCID 13566 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 촉매 | HCID 178418476 | HCID 178418476 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 생성물 | 4-(3-Bromophenyl)but-3-yn-1-ol | HCID 21895442 | 92% |
반응 단계
A solution of 10.0 gm (35.3 mmol) of 3-iodo-bromobenzene in DMF was treated with 2.95 mL (88 mmol) of 4-butyne-1-ol, 0.2 gm (1.06 mmol) of copper (I) iodide, 1.23 gm of dichlorobis(triphenylphosphine)-palladium(II), and 49 mL (0.35 mol) of triethylamine, stirred at room temperature for 18 h, poured into water and extracted with EtOAc. The combined extracts were washed sequentially with water and brine, dried over Na2SO4 and concentrated at reduced pressure. Chromatography of the resultant concentrate on silica gel with a gradient of 5% to 30% EtOAc-hexanes afforded 4-(3-bromophenyl)but-3-yn-1-ol as an orange oil, 7.3 gm (92% yield); 1H NMR (400 MHz, CDCl3) δ: 1.79 (s, 1H), 2.67 (t, 2H, J=6.3 Hz), 3.80 (t, 2H, J=6.3 Hz), 7.14 (t, 1H, J=7.9 Hz), 7.30 (d, 1H, J=7.9 Hz), 7.41 (m, 1H), 7.54 (t, 1H, J=1.6 Hz).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US07423158B2 |
|---|
| 출처 데이터셋 | uspto-grants-2008_09 |
|---|
| ORD ID | ord-cbe3e1baed484ad6aa1b66bc899ccbd9 |
|---|
| 출처 메모 | uspto-grants-2008_09 |
|---|
