反応式
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Si:13]([CH3:16])([CH3:15])[CH3:14])=[C:9]([F:17])[CH:8]=1.C(O[B:22]1[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]1)(C)C.C(=O)=O.CC(C)=O.Cl>C1COCC1.O>[F:17][C:9]1[CH:8]=[C:7]([B:22]2[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]2)[CH:12]=[CH:11][C:10]=1[Si:13]([CH3:16])([CH3:15])[CH3:14]参加物
反応物 5
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- -78 °C
実験手順
A solution of n-BuLi (2.5 M in hexanes; 8.5 mL, 21 mmol, 1.1 equiv) was added to a stirred solution of (4-bromo-2-fluorophenyl)trimethylsilane (4.8 g, 19 mmol, 1.0 equiv) in THF (80 mL) at −78° C. The resulting orange solution was stirred at −78° C. for 15 min. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.4 mL, 21 mmol, 1.1 equiv) was added, and the cloudy orange solution was allowed to slowly warm to 23° C., by allowing the dry ice/acetone bath to melt, and was stirred for 20 h. The reaction mixture was diluted with H2O (200 mL), adjusted to approximately pH=4 using 1 M hydrochloric acid (HCl), and extracted with CH2Cl2 (3×100 mL). The combined organic layers were dried (MgSO4), gravity filtered, and concentrated by rotary evaporation to afford the crude product, (2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)trimethylsilane, as a pale yellow semisolid (6.0 g, 99% crude yield): 1H NMR (400 MHz, CDCl3) δ 7.55 (dt, J=7.5, 1 Hz, 1H), 7.38-7.42 (m, 2H), 1.34 (s, 12H), 0.29 (d, J=1 Hz, 9H).
後処理
- temperatureto slowly warm to 23° C.
- stirringwas stirred for 20 h
- extractionextracted with CH2Cl2 (3×100 mL)
- dry with materialThe combined organic layers were dried (MgSO4), gravity
- filtrationfiltered
- concentrationconcentrated by rotary evaporation
出典と根拠
- ORDレコード
- ord-46efdeb8e7114776ba4dbd1f5d883ba1
- 出典データセット
- uspto-grants-2014_06
- 特許番号
- US08754229B2
関連ノート
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