반응식
[C:1]([Br:5])(Br)(Br)Br.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH:25]([C:28]1[CH:29]=[CH:30][C:31]([O:46][CH3:47])=[C:32]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][C:35]=2CO)[CH:33]=1)([CH3:27])[CH3:26]>C(Cl)Cl>[Br:5][CH2:1][C:35]1[CH:36]=[C:37]([C:40]([F:41])([F:42])[F:43])[CH:38]=[CH:39][C:34]=1[C:32]1[CH:33]=[C:28]([CH:25]([CH3:27])[CH3:26])[CH:29]=[CH:30][C:31]=1[O:46][CH3:47]참가 물질
실험 절차
CBr4 (112 mg, 0.211 mmol) and Ph3P (55 mg, 0.211 mmol) were added successively to a stirred solution of [5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methanol (57.1 mg, 0.176 mmol) in dry CH2Cl2 (1 mL) at 0° C. under N2. The solution was stirred at room temperature for 1 h and the reaction mixture was concentrated in vacuo to afford the crude product. This was purified by flash chromatography (Si, 12×160 mm, 0-20% EtOAc in hexanes gradient) to give 2-(bromomethyl)-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl as a colorless oil. Rf=0.95 (20% EtOAc/hexanes). LCMS calc.=387.05; found=387.0 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.83 (br s, 1H), 7.60 (dd, J=8.0, 1.3 Hz, 1H), 7.37 (d, J=8.0 Hz, 1H), 7.29 (dd, J=8.5, 2.3 Hz, 1H), 7.14 (d, J=2.3 Hz, 1H), 6.95 (d, J=8.5, 1H), 4.45 (d, J=10.6 Hz, 1H), 4.33 (d, J=10.6 Hz, 1H), 3.76 (s, 3H), 2.94 (septet, J=6.9 Hz, 1H), 1.29 (d, J=6.9 Hz, 6H).
후처리
- concentrationthe reaction mixture was concentrated in vacuo
- customto afford the crude product
- customThis was purified by flash chromatography (Si, 12×160 mm, 0-20% EtOAc in hexanes gradient)
출처 및 근거
- ORD 기록
- ord-2adeb91c96ed46a8b776dab444653a03
- 출처 데이터셋
- uspto-grants-2010_01
- 특허 번호
- US07652049B2
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