関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Nitrogen | HCID 947 | — |
| 反応物 | Dichloromethane | HCID 6344 | — |
| 反応物 | 4-Bromoanisole | HCID 7730 | — |
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | Tolylboronic acid | HCID 79799 | — |
| 触媒 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 4-Methoxy-4'-methylbiphenyl | HCID 1704759 | — |
反応手順
A mixture of 4-methylbenzeneboronic acid (10 g, 73.5 mmol), 4-bromoanisole (25 g, 134 mmol) and 2M aqueous Na2CO3 (75 mL, 150 mmol) in DMF (350 mL) was passed N2 for 15 min. [1,1′Bis(diphenylphosphino)ferrocene]dichloropalladium (II), complex with dichloromethane (1:1) (200mg, 0.24 mmol) was added and the mixture was heated at 85° C. for 4 h. After cooling to r.t., the mixture was diluted with H2O and extracted with EtOAc. The EtOAc extract was washed with brine (2×), dried (anhydrous MgSO4) and concentrated. The residue was dissolved in small amount of CH2Cl2, filtered through a short pack (˜2.5”) of silica gel in a 600 mL sintered glass funnel and washed the silica with hexanes:EtOAc (4:1). The filtrate was evaporated. The residue was swished with hexanes to give a white flake. The mother liquor was concentrated and swished again with hexanes. After 4 cycles, the combined yield of title product was 10.5 g (72% based on the boronic acid used.).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US06486141B2 |
|---|
| 出典データセット | uspto-grants-2002_11 |
|---|
| ORD ID | ord-270324e2bd524d82993aa4b233b3345f |
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| 出典メモ | uspto-grants-2002_11 |
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