Perfluorocyclopentene → Phenol

HRID 981364

反応式

HRID 981364 の反応式
[O:1](C1C(F)(F)C(F)(F)C(F)(F)C=1[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-][C:27]1[CH:32]=CC=[CH:29][CH:28]=1.[Na+].FC1(F)[C:39]([F:40])=[C:38]([F:41])[C:37]([F:43])([F:42])[C:36]1([F:45])[F:44].FF>COCCOC.CCOCC.C(N(CC)CC)C>[C:2]1([OH:1])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25]1[C:24]2[C:23](=[CH:32][CH:27]=[CH:28][CH:29]=2)[CH:22]=[CH:21][C:20]=1[OH:19].[F:43][C:37]1([F:42])[C:38]([F:41])=[C:39]([F:40])[C:36]1([F:44])[F:45]

参加物

10

反応物 4

HCID 11212PerfluorocyclopenteneHCID 24524FluorineHCID 4445035Phenolate SodiumHCID 12633348HCID 12633348、化合物

生成物 3

HCID 996PhenolHCID 86632-NaphtholHCID 12767Hexafluorocyclobutene

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8471Triethylamine溶媒

実験手順

The substitution of both vinylic halogen atoms in dihaloperfluoroalkenes by phenols or by phenoxides is as yet illustrated by a single example: under specific conditions (-40° C., mmol scale, complicated distillation) 1,2-bisphenoxy-3,3,4,4,5,5-hexafluorocyclopent-1-ene could be prepared in 76% yield from sodium phenoxide and octafluorocyclopentene in ethylene glycol dimethyl ether (see J.O.C. 45, 4429 (1980). Based on the other existing literature (for example Fluorine in Organic Chemistry, Wiley, 1973), it could not be concluded that this reaction could underlie a generally applicable synthesis principle. Thus, only monoaryloxy-perfluorocyclobutenes were obtained by reaction of phenol or 2-naphthol with hexafluorocyclobutene in ether using equimolar amounts of triethylamine (see J.A.C.S. 72, 4480 (1950).

後処理

  1. custombe concluded that this reaction

出典と根拠

ORDレコード
ord-8b189d6b195749a2befcd5b4bed5f57f
出典データセット
uspto-grants-1991_02
特許番号
US04990633

関連ノート

読み込み中…