反応 #64882

反応方程式

water

boron tribromide

methyl α-(2-methoxymethylphenyl)-β-methylacrylate

methanol

→

product

methyl α-(2-bromomethylphenyl)-β-methylacrylate

溶媒

CH2Cl2

methylene chloride

反応条件

後処理

1. 1
   その他At 0° C.
2. 2
   温度the mixture was refluxed for 2 hours
3. 3
   温度while cooling with ice
4. 4
   洗浄washed neutral with 3% strength caustic solution
5. 5
   抽出the aqueous phase was extracted with methylene chloride
6. 6
   洗浄The combined organic phases were washed with water
7. 7
   その他dried
8. 8
   その他evaporated down
9. 9
   その他The crystals which precipitated
10. 10
    その他were separated off
11. 11
    洗浄washed with a small amount of n-hexane
12. 12
    その他dried
13. 13
    その他The filtrates were evaporated down
14. 14
    その他purified chromatographically in a silica gel column (cyclohexane/MTBE: 8/1)

実験手順

At 0° C., 105.3 ml (140 mmol) of a 1.33 M boron tribromide solution in methylene chloride was dripped into 31 g (140 mmol) of methyl α-(2-methoxymethylphenyl)-β-methylacrylate in 500 ml of CH2Cl2, and the mixture was refluxed for 2 hours. 25 ml of methanol was then added, the mixture was stirred for a further 90 minutes at room temperature, hydrolyzed with water while cooling with ice, and washed neutral with 3% strength caustic solution, and the aqueous phase was extracted with methylene chloride. The combined organic phases were washed with water, dried and evaporated down. The crystals which precipitated were separated off, washed with a small amount of n-hexane and dried. The filtrates were evaporated down and purified chromatographically in a silica gel column (cyclohexane/MTBE: 8/1). A total of 31 g of product was obtained in the form of pale yellow crystals.

出典