反应 #674371

反应方程式

4-bromo-2-methylbenzoic acid

n-BuLi

DMF

4-Formyl-2-methylbenzoic acid

→

title compound

收率 40.0%

Ethyl 2-methyl-4-vinylbenzoate

收率 40.0%

溶剂

THF

反应条件

后处理

1. 1
   温度then was warmed to 25° C.
2. 2
   workup.STIRRINGstirred for 1 h
3. 3
   其他The reaction mixture was quenched with 1 N HCl solution
4. 4
   萃取extracted with EtOAc
5. 5
   洗涤The combined EtOAc extracts were washed with brine
6. 6
   干燥dried over Na2SO4
7. 7
   浓缩concentrated under reduced pressure
8. 8
   洗涤The residue was washed with n-hexane

实验过程

4-Formyl-2-methylbenzoic acid (AI15). To a stirred solution of 4-bromo-2-methylbenzoic acid (10 g, 46.4 mmol) in dry THF (360 mL) at −78° C. was added n-BuLi (1.6 M solution in hexanes; 58.17 mL, 93.0 mmol) and DMF (8 mL). The reaction mixture was stirred at −78° C. for 1 h then was warmed to 25° C. and stirred for 1 h. The reaction mixture was quenched with 1 N HCl solution and extracted with EtOAc. The combined EtOAc extracts were washed with brine and dried over Na2SO4 and concentrated under reduced pressure. The residue was washed with n-hexane to afford the title compound as a solid (3.0 g, 40%): mp 196-198° C.; 1H NMR (400 MHz, DMSO-d6) δ 13.32 (br s, 1H), 10.05 (s, 1H), 7.98 (m, 1H), 7.84 (m, 2H), 2.61 (s, 3H); ESIMS m/z 163.00 ([M−H]−).

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