Facile nucleophilic fluorination of primary alkyl halides using tetrabutylammonium fluoride in a tert-alcohol medium

Tetrahedron Letters

Volumn 51, Issue 2, 2010, Pages 432-434

  Kim, Dong Wook ^a   Jeong, Hwan Jeong ^a   Lim, Seok Tae ^a   Sohn, Myung Hee ^a  

^a Chonbuk National University   (South Korea)

Author keywords

Fluorinated compounds; Nucleophilic fluorination; Solvent effect; TBAF; tert Alcohol

Indexed keywords

2 (3 FLUOROPROPOXY)NAPHTHALENE; 2 (3 IODOPROPOXY)NAPHTHALENE; ACETONITRILE; ALCOHOL; ALKYL GROUP; FLUORIDE; HALIDE; NAPHTHALENE DERIVATIVE; NUCLEOPHILE; SOLVENT; TETRABUTYLAMMONIUM; TETRABUTYLAMMONIUM FLUORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CONTROLLED STUDY; FLUORINATION; POLARIZATION;

EID: 71049147183     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.058     Document Type: Article

References (23)

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23. Typical procedure (entry 6). TBAF (523 mg, 2.0 mmol) was added to the mixture of 2-(3-iodopropoxy)naphthalene (1a) (312 mg, 1.0 mmol) in t-amyl alcohol (5.0 mL). The mixture was stirred over 1.0 h at 70 °C. The residue was dissolved in water (5.0 mL) and extracted from the aqueous phase with ethyl ether (5.0 mL × 3). The organic layer was dried (sodium sulfate) and evaporated under reduced pressure. The flash column chromatography (5% EtOAc/hexanes) of the filtrate afforded 151 mg (74%) of 2-(3-fluoropropoxy)naphthalene (2a) as a colorless oil.