참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Ammonium Chloride | HCID 25517 | — |
| 반응물 | 4-Bromo-o-xylene | HCID 68504 | — |
| 반응물 | 4-Bromo-6,7-dihydro-8(5H)-isoquinolinone | HCID 71743380 | — |
| 반응물 | Butyllithium | HCID 178418339 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 생성물 | (rac)-4-Bromo-8-(3,4-dimethylphenyl)-5,6,7,8-tetrahydroisoquinolin-8-ol | HCID 89846267 | 64% |
반응 단계
A solution of 4-bromo-1,2-dimethylbenzene (78.6 mg, 425 μmol) in THF (1.3 mL) was cooled (−78° C.) and treated with n-BuLi (1.6 M in n-hexane, 265 μL, 425 μmol). After 15 min a solution of 4-bromo-6,7-dihydroisoquinolin-8(5H)-one (intermediate A-1[C]) (80 mg, 354 μmol) in THF (1.3 mL) was added and after 1 h the brown suspension was warmed up 0° C. The mixture was poured on aq. sat. NH4Cl-solution and extracted with EtOAc (3×). The organic layers were washed with aq. sat. NaHCO3 and aq. sat. NaCl solution, dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (1 to 2%)) gave the title compound (75 mg, 64%) as off-white foam. MS: 332.1 (M+H+, 1 Br).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US09187429B2 |
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| 출처 데이터셋 | uspto-grants-2015_11 |
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| ORD ID | ord-4ae8b7860039466bb129a7a5c10c46cf |
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| 출처 메모 | uspto-grants-2015_11 |
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