Process for selectively ortho-fluorinating substituted aromatic

Details Process for selectively ortho-fluorinating substituted aromatic Process for selectively ortho-fluorinating substituted aromatic

1992-06-01

1993-08-03

Mars, Howard T.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

570143, 570144, 570147, 564182, 564 84, 564 90, 564183, 568 28, 568156, C07C26100

Patent

active

052330745

ABSTRACT:
The invention describes a process for selectively preparing ortho-fluorinated substituted aromatic compounds wherein an aromatic compound containing a substituent capable of directing ortho metalation is contacted with a metalating reagent under reaction conditions sufficient to form an ortho-metalated substituted aromatic compound. The ortho-metalated substituted aromatic compound is reacted with an electrophilic fluorinating reagent under reaction conditions sufficient to form the desired ortho-fluorinated substituted aromatic compound which is then recovered from the reaction mixture. The process which utilizes a metalation intermediate prior to effecting the electrophilic fluorination step overcomes problems associated with prior art electrophilic fluorination processes which do not proceed through a regiospecifically controlled intermediate.

REFERENCES:
patent: 4828764 (1989-05-01), DesMarteau
patent: 5086178 (1992-02-01), Banks
N-Fluoro-N-Alkylsulfonamides: Useful Reagents for the Fluorination of Carbanions, W. E. Barnette, J. Am. Chem. Soc., 1984, 106, 452-454.
Hudlicky, Chemistry of Organic Fluorine Compounds, p. 185 (1962).
Furin et al., "New Fluorinating Agents in Organic Synthesis" (1989).
R. E. Bands and G. E. Williamson, Chem. Ind. (London) 1964.
R. E. Banks et al., J. Chem. Soc., Perkin Trans., I, 1972, 1098.
R. E. Banks et al., J. Chem. Soc., Perkin Trans. I (1988) 2805.
R. E. Banks et al., J. Fluorine Chem., (1986) 34, 281.
Aldrichimica Acta, 21 (1988) 3.
S. T. Purrington et al., Chem. Rev., 86 (1986) 997.

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