A boronic acid ester compound is a useful compound as e.g., an intermediate for synthesizing medical/agricultural drugs. The boronic acid ester compound has been manufactured generally by reacting an aryl halide and a diboron compound in the presence of a palladium catalyst (see, non-patent document 1, etc.).
However, use of a palladium catalyst has a problem. Generally, it is difficult to remove the catalyst from a product. In particular, in synthesizing medical/agricultural drugs, it is necessary to obtain a product with extremely high purity; however, if purification is repeatedly performed several times in order to increase the purity, the yield of the product significantly decreases (see, non-patent document 2, etc.).
In contrast, patent documents 1 and 2 exemplify a method for manufacturing a boronic acid ester compound using a nickel catalyst, which is easily removable by washing with water, etc. and relatively inexpensive.
However, conventional methods for manufacturing a boronic acid ester compound using a nickel catalyst described, for example, in patent documents 1 and 2 have a problem in insufficient yield.    [Patent document 1] WO 98/45265    [Patent document 2] U.S. 2003/0032838    [Non-patent document 1] Journal of Organic Chemistry 60 (23), 7508 (1995)    [Non-patent document 2] C. Someswara Rao, The Chemistry of Process Development in Fine Chemical & Pharmaceutical Industry Second Edition (John Wiley & sons, LTD, p. 981)