Perfluorocyclopentene → Phenol

HRID 981364

반응식

HRID 981364 반응식
[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]

참가 물질

10

반응물 4

HCID 11212PerfluorocyclopenteneHCID 24524FluorineHCID 4445035Phenolate SodiumHCID 12633348HCID 12633348, 화합물

생성물 3

HCID 996PhenolHCID 86632-NaphtholHCID 12767Hexafluorocyclobutene

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 80711,2-Dimethoxyethane용매HCID 8471Triethylamine용매

실험 절차

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).

후처리

  1. custombe concluded that this reaction

출처 및 근거

ORD 기록
ord-8b189d6b195749a2befcd5b4bed5f57f
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04990633

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