A Simple Method for the Conversion of Adamantyl, Benzyl and Benzyhydryl Alcohols to Their Corresponding Bromides and Chlorides and the Transhalogenation of Adamantyl, Benzyl, Benzhydryl and Tertiary Alkyl Bromides and Chlorides

Development of a Rapid Scale-Up Synthesis of (S)-N-(8-((2-Amino-2,4-dimethylpentyl)oxy)-5H-chromeno[3,4-c]pyridin-2-yl)acetamide, a Potent Adaptor-Associated Kinase 1 Inhibitor

“…An appealing approach for the synthesis of 1 involved nucleophilic cleavage of 1,2-cyclic sulfamidate 18 with phenol 17 − followed by hydrogenation that would simultaneously remove the Cbz group and reduce the olefin (Scheme ). Phenol 17 was anticipated to be obtained from 19 through the concomitant BBr 3 -promoted bromination of the primary alcohol of 19 , double demethylation of the dimethoxy benzene, and subsequent base-mediated intramolecular cyclization of the alkoxide with the benzyl bromide . Alcohol 19 could be prepared in three steps from readily available methyl 4,6-dichloronicotinate ( 22 ) via selective amidation to form 21 , followed by Suzuki coupling to yield 20 , and finally, reduction of ester 20 .…”

The umpolung of substituent effect in nucleophilic aromatic substitution. A new approach to the synthesis of N,N-disubstituted melamines (triazine triskelions) under mild reaction conditions

“…19 The distillate was washed with 1 M aqueous KHSO 4 (10 mL) dried with CaCl 2 , filtered, and redistilled yielding benzyl chloride (6h) (2.33 g, 92%); bp¼176 C, lit. 25 (m, 24H). 13 …”

Boron Trihalide Mediated Haloallylation of Aryl Aldehydes and Its Application to the Preparation of (E)-1,3-Dienes

“…4 Boron trihalides are used as halogenation reagents in conversions of alcohols into the corresponding halides. 5 Halogen exchange between alkyl halides and boron trihalides has also been reported. 6 Boron trihalides readily form crystalline complexes with carbonyl compounds.…”