Preparation and structure determination of trimethylamine-dibromocarboxyborane esters

Eli Shalom; Khuloud Takrouri; Israel Goldberg; Jehoshua Katzhendler; Morris Srebnik

doi:10.1021/om049618y

Preparation and structure determination of trimethylamine-dibromocarboxyborane esters

Eli Shalom, Khuloud Takrouri, Israel Goldberg, Jehoshua Katzhendler, Morris Srebnik^*

^*Corresponding author for this work

School of Chemistry

Hebrew University of Jerusalem

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

We have developed a new method for the preparation of esters of trimethylamine-dibromocarboxyborane (Me₃N·BBr ₂COOR), from trimethylamine-carboxyborane, in a one-pot reaction. The reaction involves the treatment of trimethylamine-carboxyborane with 2.5 equiv of Br₂ in the appropriate alcohol for 4 h at 0°C, for compounds 1-5 (R = Me, Et, n-Pr, CH₂CH₂Cl, CH ₂CF₃), and 5 equiv of Br₂ for 8 h under the same conditions, for compounds 6-8 (R = n-Bu, i-Bu, i-Pe). Compounds 1-5 were obtained in high purity and in essentially quantitative yields (∼99%). Compounds 6-8 were purified from traces of monobromo product and the alcohol by column chromatography. Molecular structures for the compounds 2, 6, and 7 were determined by X-ray crystallography.

Original language	English
Pages (from-to)	4396-4399
Number of pages	4
Journal	Organometallics
Volume	23
Issue number	19
DOIs	https://doi.org/10.1021/om049618y
State	Published - 13 Sep 2004

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title = "Preparation and structure determination of trimethylamine-dibromocarboxyborane esters",

abstract = "We have developed a new method for the preparation of esters of trimethylamine-dibromocarboxyborane (Me3N·BBr 2COOR), from trimethylamine-carboxyborane, in a one-pot reaction. The reaction involves the treatment of trimethylamine-carboxyborane with 2.5 equiv of Br2 in the appropriate alcohol for 4 h at 0°C, for compounds 1-5 (R = Me, Et, n-Pr, CH2CH2Cl, CH 2CF3), and 5 equiv of Br2 for 8 h under the same conditions, for compounds 6-8 (R = n-Bu, i-Bu, i-Pe). Compounds 1-5 were obtained in high purity and in essentially quantitative yields (∼99%). Compounds 6-8 were purified from traces of monobromo product and the alcohol by column chromatography. Molecular structures for the compounds 2, 6, and 7 were determined by X-ray crystallography.",

author = "Eli Shalom and Khuloud Takrouri and Israel Goldberg and Jehoshua Katzhendler and Morris Srebnik",

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AU - Shalom, Eli

AU - Takrouri, Khuloud

AU - Goldberg, Israel

AU - Katzhendler, Jehoshua

AU - Srebnik, Morris

PY - 2004/9/13

Y1 - 2004/9/13

N2 - We have developed a new method for the preparation of esters of trimethylamine-dibromocarboxyborane (Me3N·BBr 2COOR), from trimethylamine-carboxyborane, in a one-pot reaction. The reaction involves the treatment of trimethylamine-carboxyborane with 2.5 equiv of Br2 in the appropriate alcohol for 4 h at 0°C, for compounds 1-5 (R = Me, Et, n-Pr, CH2CH2Cl, CH 2CF3), and 5 equiv of Br2 for 8 h under the same conditions, for compounds 6-8 (R = n-Bu, i-Bu, i-Pe). Compounds 1-5 were obtained in high purity and in essentially quantitative yields (∼99%). Compounds 6-8 were purified from traces of monobromo product and the alcohol by column chromatography. Molecular structures for the compounds 2, 6, and 7 were determined by X-ray crystallography.

AB - We have developed a new method for the preparation of esters of trimethylamine-dibromocarboxyborane (Me3N·BBr 2COOR), from trimethylamine-carboxyborane, in a one-pot reaction. The reaction involves the treatment of trimethylamine-carboxyborane with 2.5 equiv of Br2 in the appropriate alcohol for 4 h at 0°C, for compounds 1-5 (R = Me, Et, n-Pr, CH2CH2Cl, CH 2CF3), and 5 equiv of Br2 for 8 h under the same conditions, for compounds 6-8 (R = n-Bu, i-Bu, i-Pe). Compounds 1-5 were obtained in high purity and in essentially quantitative yields (∼99%). Compounds 6-8 were purified from traces of monobromo product and the alcohol by column chromatography. Molecular structures for the compounds 2, 6, and 7 were determined by X-ray crystallography.

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Preparation and structure determination of trimethylamine-dibromocarboxyborane esters

Abstract

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