Synthesis of organic bromides via organotrifluoroborates

Organometallics

Volumn 23, Issue 19, 2004, Pages 4519-4521

  Kabalka, George W ^a   Mereddy, Arjun Reddy ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCIDAL AGENTS; ORGANOTRIFLUOROBORATES; REAGENTS; REGIOSLECTIVITY;

BROMINE COMPOUNDS; CATALYSIS; DERIVATIVES; DRUG PRODUCTS; ESTERS; NUCLEAR MAGNETIC RESONANCE; POTASSIUM COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ORGANOMETALLICS;

EID: 4544244426     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049685s     Document Type: Article

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32. General procedure: to a solution of potassium organotrifluoroborate (1.0 mmol) in 50% aqueous tetrahydrofuran (5 mL), contained in a round-bottomed flask, was added chloramine-T (1.2 mmol), followed by sodium bromide (1.2 mmol). The resulting solution was stirred at room temperature for the required length of time (Tables 1-3). The mixture was extracted into ethyl acetate (3 × 25 mL), and the combined organic extracts were washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The product was purified by column chromatography over silica gel using petroleum ether/ethyl acetate (98/2). The products were identified by comparison of physical and spectral properties with literature values. (Note that 0.03 mmol of trifluoroacetic acid was added for entries 5 and 6 (Table 1) and entries 1-5 (Table 2).)
33. Example of large-scale procedure: to a solution of potassium naphthyltrifluoroborate (25.0 mmol, 5.89 g) in 50% aqueous tetrahydrofuran (100 mL), contained in a round-bottomed flask, was added chloramine-T (30.0 mmol, 8.50 g) followed by sodium bromide (30.0 mmol, 3.10 g). The resultant solution was stirred at room temperature for 10 min, and then the mixture was extracted into toluene (3 × 50 mL). The combined abstracts were washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to yield essentially pure 1-bromonaphthylene. Vacuum distillation produced 4.34 g (84%) of analytically pure product.