反応 #680909

反応方程式

3-bromo-2-fluorobenzaldehyde

pyridin-2-ylmagnesium bromide

→

title compound

収率 22.5%

(3-Bromo-2-fluorophenyl)(pyridin-2-yl)methanol

収率 22.5%

溶媒

CH2Cl2

THF

反応条件

後処理

1. 1
   温度to warm to room temperature slowly over 2 hr
2. 2
   その他The reaction quenched with a saturated aqueous solution of NH4Cl
3. 3
   workup.ADDITIONThe reaction mixture was diluted with CH2Cl2
4. 4
   その他Layers were separated
5. 5
   抽出The aqueous phase was extracted with CH2Cl2 (2×)
6. 6
   乾燥dried over Na2SO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated
9. 9
   その他to afford a yellow residue
10. 10
    その他chromatographed
11. 11
    その他Purification of the crude material by silica gel chromatography
12. 12
    その他an ISCO machine (40 g column, 40 mL/min, 1-40% EtOAc in hexanes over 25 min, tr=16 min)

実験手順

To a solution of 3-bromo-2-fluorobenzaldehyde (0.250 g, 1.231 mmol) in THF (5.35 mL) cooled to −78° C. was added pyridin-2-ylmagnesium bromide (5.91 mL, 1.478 mmol). The reaction mixture was maintained at −78° C. for at least 1 hr, then allowed to warm to room temperature slowly over 2 hr. The reaction quenched with a saturated aqueous solution of NH4Cl. The reaction mixture was diluted with CH2Cl2. Layers were separated. The aqueous phase was extracted with CH2Cl2 (2×). The organics were combined, dried over Na2SO4, filtered, and concentrated to afford a yellow residue. The crude material was dissolved in a minimal amount CH2Cl2 and chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (40 g column, 40 mL/min, 1-40% EtOAc in hexanes over 25 min, tr=16 min) gave the title compound (78 mg, 0.276 mmol, 22.45% yield) as a yellow residue.

出典