A mild and efficient method for converting alcohols and tetrahydropyranyl ethers to bromides with inversion of configuration

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 1955-1956

  Tanaka, Akira ^a   Oritani, Takayuki ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BROMINE DERIVATIVE; ETHER DERIVATIVE; TETRAHYDROFURAN;

ARTICLE; BROMINATION; SYNTHESIS; TECHNIQUE;

EID: 0031575739     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00232-3     Document Type: Article

References (9)

1. 1. Wade, L. G. Jr.; Compendium of Organic Synthetic Methods Vol. 8; Wiley-Interscience: New York, 1995 and earlier volumes in the series.
2. 2. Larock, R. C.; Comprehensive Organic Transformations; VCH Publishers: New York, 1989.
3. 3. Hughes, D. L.; Organic Reactions, 1992, 42, 335-656.
4. 4. Kocienski, P. J.; Cernigliaro, G.; Feldstein, G.; J. Org. Chem., 1977, 42, 353-354.
5. 3 afforded pure 1 as golden yellow crystals, which could be stored at -10° C for several months.
6. 2 column chromatography using hexane led to 3a-bromocholestane (13)(388 mg, 86% yield), together with 2,4,6-tribromophenol (320 mg, 97%).
7. 7. Tsubota, M.; Iso M.; Suzuki, K.; Bull. Chem. Soc. Jpn., 1972, 45, 1252-1253.
8. 8. Hughes, D. L.; Organic Preparations and Procedures Int., 1996, 28, 127-164.
9. 9. Makabe, H.; Tanaka, A.; Oritani, T.; Biosci. Biotech. Biochem., 1993, 57, 1028-1029.