2-(Benzyloxy)-6-bromonaphthalene → 2-(5,5,6,6,7,7,8,8,8-Nonafluoro-octyl)-buta-1,3-diene

반응식

[F:1][C:2]([F:29])([C:19]([F:28])([F:27])[C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])[CH2:3][CH2:4][CH2:5][CH2:6]OC1(C)C=CC(S([O-])(=O)=O)=CC1.[CH2:30](OC1C=CC2C(=CC=C(Br)C=2)C=1)[C:31]1C=CC=[CH:33][CH:32]=1>C1COCC1.[Cu]Br>[F:29][C:2]([F:1])([C:19]([F:27])([F:28])[C:20]([F:25])([F:26])[C:21]([F:22])([F:23])[F:24])[CH2:3][CH2:4][CH2:5][CH2:6][C:31]([CH:32]=[CH2:33])=[CH2:30]

참가 물질

실험 절차

To a solution of 4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyl)-tosylate (10), (1 equi) and copper (I) bromide (0.05 equi.) in THF (2 mL/mmole), a solution of buta-1,3-diene-2-magnesium chloride, prepared as described in (3), (38) (0.5M in THF) (1.3 equi.) was added at ice temperature over a period of 20 min. The reaction mixture was stirred at room temperature for 24 h, quenched with 5% aqueous ammonium chloride (1 mL/mmole), extracted with hexane, washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (hexane) gave 2-(5,5,6,6,7,7,8,8,8-nona fluoro-octyl)-buta-1,3-diene (39) a colorless oil (96%).