问题：急求2-氟噻吩的合成路线
类型：求助 (悬赏分:3分)
提问：dhuedu
等级：▲
版块：有机化学问题(jimuwei,fpcwin1211,netpanda,yjgzfl,Ftian,)
信誉：95%
回复：3
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时间：2008-07-27 11:41:18 编辑加入/取消收藏订制/取消短消息举报该贴

急求2-氟噻吩的合成路线，请发到liguowei1@163.com,谢谢！

回复人：dhuedu,▲ (热爱有机化学，痴迷有机合成) 时间：2008-08-24 10:35:28 编辑	1楼
谢谢，谢谢！

回复人：xuhuadong,▲▲ (永远求知) 时间：2008-07-28 12:28:44 编辑

2楼

To a solution of thiophene (4.8 mL, 60 mmol) in dry ET2O (200 mL) at 0 .deg.C was added N-BULI (70 mL, 66 mmol, 0.95 M in hexane) dropwise, and the solution was stirred for 1 hour AT-5-0 .deg.C. Then the temperature was adjusted TO-70 .deg.C, and a solution of (PHS02) 2NF (28.4 g, 90 mmol) in dry tetrahydrofuran (200 ML) was added, while maintaining the temperature BELOW-50 .deg.C. The resultant mixture was then slowly allowed to warm to room temperature overnight, 2 N NAOH (300 mL) was added, the mixture was filtered, and the organic layer was washed with 2 N NAOH (2 x 300 mL) and saturated NH4C1 (300 ML) and was then dried over NA2S04. Distillation using a 40 cm Vigreux column removed most of the Et2O, and final co- distillation with heptane (50 ML) yielded a solution of 20.7 mmol 2-fluorothiophene and 4.6 mmol thiophene (determined BY 1H NMR using 200 IL OF DME as internal standard) in ca. 100 mL of tetrahydrofuran and heptane (bp. 60-100 .deg.C). This solution was cooled to 0 .deg.C and N-BULI (44 mL, 41 mmol, 0.95 M in hexane) was added dropwise. After 1 hour, a solution of DMF (4.8 ML, 62 mmol) in ET20 (15 mL) was added dropwise, and stirring was continued for another 1 hour at 0 .deg.C. The reaction was then quenched with saturated NH4C1 (200 ML) and extracted with Et2O (2 x 200 mL), and the extract was dried over NA2S04. MOST of the solvent was removed by distillation at atmospheric pressure (40 cm Vigreux column) and the dark residue was then vacuum distilled to yield a ca. 10: 1 mixture of 5-fluoro-thiophene-2- carbaldehyde and thiophene-2-carbaldehyde (bp. 78-79 .deg.C, 25 mmHg) as a golden oil (1.32 g, 44percent). This mixture was used without further purification.
Frontpage/Claim: 342723; Fulltext: LitLink; Patent; H. LUNDBECK A/S; Publ.: WO2004/58739 A1 (2004/07/15), Appl.: WO2003-DK906 (2003/12/18)

回复人：xiaoyaolcl,★★★★★ (由于爱好,所以从事) 时间：2008-07-28 17:37:32 编辑	3楼
已经打分了！

得分人：xuhuadong :3,

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