참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Sodium Carbonate | HCID 10340 | — |
| 반응물 | Triphenylphosphine | HCID 11776 | — |
| 반응물 | Tolylboronic acid | HCID 79799 | — |
| 반응물 | Ethyl 2-bromobenzoate | HCID 80186 | — |
| 반응물 | 4'-Methyl-biphenyl-3-carboxylic acid ethyl ester | HCID 10728754 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 촉매 | palladium(II) acetate | HCID 167845 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 생성물 | 4'-Methyl-biphenyl-2-carboxylic acid ethyl ester | HCID 10922668 | 99% |
반응 단계
4′-Methyl-biphenyl-2-carboxylic acid ethyl ester was prepared in a similar fashion to 4′-methyl-biphenyl-3-carboxylic acid ethyl ester as described. Ethyl 2-bromobenzoate (5.0 g, 21.83 mmol, 1 eq.) and 4-methylbenzeneboronic acid (3.12 g, 22.92 mmol, 1.05 eq.) in THF and aqueous 2M sodium carbonate (24 mL, 2.2 eq.) were treated with palladium(II) acetate (0.49 g, 2.18 mmol, 10 mol %), triphenylphosphine (2.52 g, 9.59 mmol, 4.4×Pd), and copper(I) iodide (0.14 g). When complete, the reaction was worked up as described leaving an orange oil, which was purified, via silica gel flash chromatography using a step gradient of EtOAc in hexane as the mobile phase. Fractions containing the product were pooled leaving 4′-methyl-biphenyl-2-carboxylic acid ethyl ester (5.24 g, 99% yield) as a yellow oil.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US07132456B2 |
|---|
| 출처 데이터셋 | uspto-grants-2006_11 |
|---|
| ORD ID | ord-feaea149df474be7ab27d2581df2de54 |
|---|
| 출처 메모 | uspto-grants-2006_11 |
|---|
