The Chlorination of Dibenzofuran and Some of Its Derivatives

Oita, Katashi; Johnson, Robert G.; Gilman, Henry

doi:10.1021/jo01123a018

Cited by 14 publications

(3 citation statements)

References 8 publications

(16 reference statements)

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“…112.0 ppm. The spectroscopic data match with those previously described [58]. 6-Bromo-1,1-dichloronaphthalen-2(1H)-one(23): The following compound was obtained according to the general procedure for chlorination by using 6-Bromo-2-napthol in 72 % yield as orange solid.…”

supporting

confidence: 74%

In Situ Formed I^III‐Based Reagent for the Electrophilic ortho‐Chlorination of Phenols and Phenol Ethers: The Use of PIFA‐AlCl₃ System

et al. 2018

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A new and in situ formed reagent generated by mixing PIFA {bis[(trifluoroacetoxy)iodobenzene]} and AlCl3 was introduced in the organic synthesis for the direct and highly regioselective ortho‐chlorination of phenols and phenol ethers. An efficient electrophilic chlorination for these electron‐rich arenes as well as the scope of the reaction are described herein. An easy, practical, and open‐flask reaction allowed us to introduce a chlorine atom, which is a highly important functional group in organic synthesis. The reproducibility of our method has been demonstrated on gram‐scale by carrying out the reaction in 6‐bromo‐2‐naphthol. This halogenation reaction also proceeds in excellent conditions by first preparing the iodine(III)‐based chlorinating reagent. Our new chlorinating reagent can be stored at least for two weeks at 4 °C without losing its reactivity.

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confidence: 74%

In Situ Formed I^III‐Based Reagent for the Electrophilic ortho‐Chlorination of Phenols and Phenol Ethers: The Use of PIFA‐AlCl₃ System

et al. 2018

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“…3CDF was produced by nitration of dibenzofuran, diazotation and chlorination by the Sandmeyer reaction [9,10].…”

Section: Methodsmentioning

confidence: 99%

Transformation of 3-chlorodibenzofuran by Pseudomonas sp. HH69

Harms¹

1991

FEMS Microbiology Letters

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The dibenzofuran-degrading bacterial strain Pseudomonas sp. HH69 showed high oxidative activity towards 3-chlorodibenzofuran (3CDF). During the co-metabolic turnover of 3CDF large amounts of 4-chlorosalicylate and temporarily small amounts of salicylate were excreted. Simultaneously a yellow colour appeared due to the excretion of two polar products. Conversion of 3CDF by a mutant, derived from Pseudomonas sp. HH69 and defective in 2,3-dihydroxybiphenyl-1,2-dioxygenase led to the formation of equal quantities of 4'-chloro-2,2',3-trihydroxybiphenyl (4'CTHBP) and 4-chloro-2,2',3-trihydroxybiphenyl (4CTHBP). Crude extracts of the wild type transformed 4'CTHBP to 4-chlorosalicylate, whilst 4CTHBP was transformed to salicylate. Hence, we propose a non-selective initial attack on both aromatic rings of 3CDF and a degradative pathway for the resulting chlorotrihydroxybiphenyls.

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“…[7c] However, in most cases the reported yields of purified products are below 40 %, limiting the use in preparative organic chemistry. Moreover, double halogenation occurred frequently for some derivatives, showing a lack of regioselectivity . This drawback was also reported for the synthesis of 1‐bromo‐dibenzofuran‐2‐ol more recently.…”

Section: Introductionmentioning

confidence: 83%

Rapid Access to Bi‐ and Tri‐Functionalized Dibenzofurans and their Application in Selective Suzuki–Miyaura Cross Coupling Reactions

et al. 2018

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Syntheses of 1,2‐, 1,3‐, 1,4‐, 1,8‐, 2,4‐, 3,4‐, 4,8‐, 1,2,4‐, 1,2,8‐ and 1,3,4‐functionalized dibenzofurans in few steps with good to excellent yields starting from dibenzofuran‐1‐ol or ‐4‐ol are presented. These rapidly accessible bi‐ or tri‐functionalized building blocks are of great interest for the synthesis of bioactive substances or functional material development. Furthermore, for intermediates containing both a bromine and a triflate moiety, a selective mono‐substitution by means of Suzuki–Miyaura reaction (SMR) is described.

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The Chlorination of Dibenzofuran and Some of Its Derivatives

Cited by 14 publications

References 8 publications

In Situ Formed I^III‐Based Reagent for the Electrophilic ortho‐Chlorination of Phenols and Phenol Ethers: The Use of PIFA‐AlCl₃ System

In Situ Formed I^III‐Based Reagent for the Electrophilic ortho‐Chlorination of Phenols and Phenol Ethers: The Use of PIFA‐AlCl₃ System

Transformation of 3-chlorodibenzofuran by Pseudomonas sp. HH69

Rapid Access to Bi‐ and Tri‐Functionalized Dibenzofurans and their Application in Selective Suzuki–Miyaura Cross Coupling Reactions

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The Chlorination of Dibenzofuran and Some of Its Derivatives

Cited by 14 publications

References 8 publications

In Situ Formed IIII‐Based Reagent for the Electrophilic ortho‐Chlorination of Phenols and Phenol Ethers: The Use of PIFA‐AlCl3 System

In Situ Formed IIII‐Based Reagent for the Electrophilic ortho‐Chlorination of Phenols and Phenol Ethers: The Use of PIFA‐AlCl3 System

Transformation of 3-chlorodibenzofuran by Pseudomonas sp. HH69

Rapid Access to Bi‐ and Tri‐Functionalized Dibenzofurans and their Application in Selective Suzuki–Miyaura Cross Coupling Reactions

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Product

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In Situ Formed I^III‐Based Reagent for the Electrophilic ortho‐Chlorination of Phenols and Phenol Ethers: The Use of PIFA‐AlCl₃ System

In Situ Formed I^III‐Based Reagent for the Electrophilic ortho‐Chlorination of Phenols and Phenol Ethers: The Use of PIFA‐AlCl₃ System