Dibenzothiophene → Anthra[2,3-b]benzo[d]thiophene-7,12-dione

HRID 68179

반응식

C1C2C3C=C4C(C=C5C(=C4)C=CC=C5)=CC=3SC=2C=CC=1.[CH:22]1[C:30]2[C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[S:27][C:26]=2[CH:25]=[CH:24][CH:23]=1.[C:35]1(=O)[O:40][C:38](=[O:39])[C:37]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:36]12.[Cl-].[Al+3].[Cl-].[Cl-].P(Cl)(Cl)(Cl)(Cl)Cl>>[CH:31]1[C:29]2[C:30]3[CH:22]=[C:23]4[C:24]([C:35](=[O:40])[C:36]5[CH:44]=[CH:43][CH:42]=[CH:41][C:37]=5[C:38]4=[O:39])=[CH:25][C:26]=3[S:27][C:28]=2[CH:34]=[CH:33][CH:32]=1

참가 물질

반응물 5

HCID 3023Dibenzothiophene

HCID 6811Phthalic Anhydride

HCID 24819Phosphorus pentachloride

HCID 6428178Anthra[2,3-b]benzo[d]thiophene

HCID 6451240Aluminum(III) Chloride

생성물 1

HCID 282271Anthra[2,3-b]benzo[d]thiophene-7,12-dione

실험 절차

The synthesis of the anthra[2,3-b]benzo[d]thiophene unit with added trialkylsilylethynyl groups is shown in Scheme 1. Commercially available dibenzothiophene undertakes a Friedel-Crafts reaction with phthalic anhydride to give 2-(2′-carboxybenzoyl)dibenzothiaphene. The acid is then treated with aluminum chloride and phosphorus pentachloride to yield anthra[2,3-b]benzo[d]thiophene-7,12-dione. The dione is alkylated with the lithium salt of the trialkylsilylacetylene reagent followed by aromatisation utilising tin (II) chloride under acidic conditions to give 7,12-bis(trialkylsilylethynyl)anthra[2,3-b]benzo[d]thiophene.

후처리

customto give 2-(2′-carboxybenzoyl)dibenzothiaphene

출처 및 근거

ORD 기록: ord-9c5acdcb6d1b4dbdb62c274da4228eb1
출처 데이터셋: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08821762B2

연결된 노트

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