4-Benzyloxy-3-methylbenzeneboronic acid

4-Bromo-1-benzyloxy-2-methyl-benzene (6.9 g; 25 mmol) is dissolved in tetrahydrofuran (37.5 ml; dried over a molecular sieve) and the solution is cooled to -78° C. A 1.6 M n-butyllithium solution in n-hexane (17 ml; 27.5 mmol) is added dropwise in the course of 30 minutes such that the temperature does not rise above -70° C. After a further 10 minutes at this temperature, trimethyl borate (8.3 ml; 75 mmol) is added dropwise in the course of 25 minutes at below -70° C. The reaction mixture is allowed to warm slowly to room temperature overnight. It is then cooled to 0° C. and an aqueous 1 N hydrochloric acid solution is added dropwise. The reaction mixture is diluted with water and ethyl acetate, the phases are separated and the aqueous phase is re-extracted with ethyl acetate. The combined organic phases are washed successively with water and a saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered with suction and concentrated. [00235] Yield: 3.95 g (65percent) 4-benzyloxy-3-methyl-phenylboron acid as a white powder. [00236] MS(ISN): 301.2 (M-H)

suzuki reaction

Molecular Weight:242.08
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:242.1114245
Monoisotopic Mass:242.1114245
Topological Polar Surface Area:49.7
Heavy Atom Count:18
Complexity:241
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes