反応 #721252

反応方程式

2,6-dimethylbromobenzene

nBuLi

2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

→

2-(2,6-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

溶媒

反応条件

後処理

1. 1
   workup.STIRRINGThe resulting mixture was stirred overnight at room temperature
2. 2
   その他evaporated to dryness
3. 3
   workup.ADDITIONThe residue was poured into 500 ml of water, crude product
4. 4
   抽出was extracted with 3×200 ml of ethyl acetate
5. 5
   抽出The combined organic extract
6. 6
   乾燥was dried over Na2SO4
7. 7
   その他evaporated to dryness

実験手順

To a solution of 35.0 g (0.19 mol) of 2,6-dimethylbromobenzene cooled to −78° C., 76 ml (0.19 mol) of 2.5 M nBuLi in hexanes was added for 40 min. The resulting mixture was stirred at this temperature for 1 h, then 35.2 g (0.19 mol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added. The resulting mixture was stirred overnight at room temperature and then evaporated to dryness. The residue was poured into 500 ml of water, crude product was extracted with 3×200 ml of ethyl acetate. The combined organic extract was dried over Na2SO4 and then evaporated to dryness. Yield 19.5 g (53%) of yellow crystalline solid. Anal. calc. for C14H21BO2: C, 72.44; H, 9.12. Found: C, 72.78; H, 9.45. 1H NMR (CDCl3): δ 7.12 (t, J=7.7 Hz, 1H, 4-H), 6.94 (d, J=7.7 Hz, 2H, 3, 5-H), 2.40 (s, 6H, 2, 6-Me), 1.38 (s, 12H, Bpin).

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