The metalation of fluoroanisoles: optional regioselectivity due to metal mediated control

2- And 4-Fluoroanisole undergo hydrogen/metal exchange at the position next to the alkoxy moiety if n-BuLi or tert-BuLi is used and at the position next to the halogen atom if the stoichiometric mixt. of butyllithium and potassium tert-butoxide serves as the reagents. 3-Fluoroanisole is always attacked at the position flanked by the 2 hetero-substituents. [on SciFinder (R)]


Published in:
Synlett, 10, 731-2
Year:
1991
Keywords:
Note:
CAN 116:20731
25-9
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0936-5214
written in English.
68359-59-1P; 137654-22-9P (2-Fluoro-5-phenoxybenzoic acid) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, from regioselective lithiation and carboxylation of Ph fluorophenyl ether); 367-83-9P (2-Fluoro-5-methoxybenzoic acid); 394-04-7P (5-Fluoro-2-methoxybenzoic acid); 106428-05-1P (3-Fluoro-2-methoxybenzoic acid); 137654-20-7P (2-Fluoro-3-methoxybenzoic acid); 137654-21-8P (2-Fluoro-6-methoxybenzoic acid) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, from regioselective lithiation and carboxylation of fluoroanisole); 321-28-8 (2-Fluoroanisole); 330-84-7; 456-49-5 (3-Fluoroanisole); 459-60-9 (4-Fluoroanisole) Role: RCT (Reactant), RACT (Reactant or reagent) (regioselective lithiation and carboxylation of); 109-72-8P (Butyllithium) Role: RCT (Reactant), PREP (Preparation), RACT (Reactant or reagent) (regioselective lithiation by, of fluoroanisoles); 594-19-4 (tert-Butyllithium); 598-30-1 Role: RCT (Reactant), RACT (Reactant or reagent) (regioselective lithiation by, of fluoroanisoles)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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