反応 #564229

反応方程式

sodium carbonate

ammonia

methyl 5-bromonicotinate

sodium carbonate

(4-methoxyphenyl)boric acid

→

methyl 5-(4-methoxyphenyl)nicotinate

収率 24.7%

溶媒

methylene chloride

toluene

methanol

反応条件

後処理

1. 1
   workup.ADDITIONwere added
2. 2
   抽出extraction
3. 3
   その他The organic layer was separated
4. 4
   その他the solvent was evaporated
5. 5
   洗浄The column was eluted with a 3:7 mixture of ethyl acetate and hexane
6. 6
   その他The solvent was evaporated from the eluate

実験手順

2.16 g of methyl 5-bromonicotinate and 350 mg of tetrakis(triphenylphosphine)palladium were dissolved in 20 ml of toluene, and under a nitrogen current, 10 ml of a 2M aqueous solution of sodium carbonate and a suspension of 1.82 g of (4-methoxyphenyl)boric acid in 5 ml of methanol were added. The mixture was stirred at a bath temperature of 80° C. for 12 hours. To the reaction solution were added 100 ml of methylene chloride, 50 ml of a 2M aqueous solution of sodium carbonate and 5 ml of conc. aqueous ammonia to perform extraction. The organic layer was separated, and the solvent was evaporated. The residue was subjected to silica gel column chromatography. The column was eluted with a 3:7 mixture of ethyl acetate and hexane. The solvent was evaporated from the eluate to give 600 mg (yield 24.7%) of methyl 5-(4-methoxyphenyl)nicotinate as colorless needles having a melting point of 99° to 101° C.

出典