苯胺-1-13C → 间苯二胺

HRID 257707笔记

反应方程式

HRID 257707 反应方程式
FF.[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].C1([N+:25]#N)C=CC=CC=1.[F:27][B-](F)(F)F.NC1C=CC=CC=1.[F-].C1([N+]#N)C=CC=CC=1>F>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:27])[CH:5]=1.[C:14]1([NH2:25])[CH:15]=[CH:16][CH:17]=[C:12]([NH2:11])[CH:13]=1

参与物

10

反应物 7

HCID 6115苯胺-1-13CHCID 8870盐酸苯胺HCID 10008氟苯2 次HCID 24524氟HCID 26255四氟代硼酸根HCID 60992Benzenediazonium chlorideHCID 14533789Benzenediazonium fluoride

产物 2

HCID 7935间苯二胺HCID 97411,3-二氟苯

试剂、催化剂与溶剂 1

HCID 14917氢氟酸溶剂

实验过程

Fluorobenzenes have hitherto been prepared from the corresponding substituted anilines by diazotization and subsequent replacement of the diazo group by fluorine. Thus the preparation of fluorobenzene by diazotization of aniline hydrochloride, conversion of the resulting benzenediazonium chloride into the tetrafluoroborate and subsequent heating has long been known (G. Balz and G. Schiemann, Ber. 60 (1927) 1188; D. T. Flood, Org. Synth. Coll. Vol II (1943) 295). In addition, the preparation of fluorobenzene by diazotization of aniline in anhydrous hydrogen fluoride at 0° C. with subsequent decomposition of the resulting benzenediazonium fluoride at 20° C. is also described (Kirk-Othmer, Encyclopedia of Chemical Technology, 3rd ed. Vol. 10, p. 908). 1,3-Difluorobenzene could be obtained analogously in a 31% yield, relative to m-phenylenediamine as starting compound, by heating benzene-1,3-bis-diazonium tetrafluoroborate (G. Schiemann and R. Pillarsky, Ber. 62 (1929) 3035-3043, especially 3029). The diazotization of 3-fluoroaniline in anhydrous hydrogen fluoride in the presence of either ammonium fluoride or tertiary amines or dimethyl sulfoxide produced in each case 1,3-difluorobenzene in a yield of 46 to 73% (U.S. Pat. No. 4,075,252 and U.S. Pat. No. 4,096,196).

后处理

  1. temperaturesubsequent heating

来源与证据

ORD记录
ord-1930399397974ff2b32f0c38d68ddfc8
来源数据集
uspto-grants-1993_11
专利号
US05264094

反应笔记

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