1,2-DIHYDRO-NAPHTHALENE-3-BORONIC ACID synthesis

5synthesis methods

Product Name:1,2-DIHYDRO-NAPHTHALENE-3-BORONIC ACID
CAS Number:521917-51-1
Molecular formula:C10H11BO2
Molecular Weight:174

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Yield:521917-51-1 60%

Reaction Conditions:

Stage #1: 3-bromo-1,2-dihydroxynaphthalenewith tert.-butyl lithium in diethyl ether;pentane at -65; for 0.5 h;
Stage #2: Triisopropyl borate in diethyl ether;pentane at -65 - 20;
Stage #3: with hydrogenchloride in diethyl ether;water;pentane at 20;

Steps:

137 EXAMPLE 137; 3,4-Dihydro-naphthalene-2-boronic Acid

A solution of 3-bromo-1,2-dihydro-naphthalene (7.7 g, 37 mmol) (Adamczyk, M.; Watt, D. S.; Netzel, D. A. J. Org. Chem. 1984, 49, 4226-4237) in diethylether (370 ml) was cooled in a dry ice bath and tert.-butyllithium solution (50 ml of a 1.5 M solution in pentane) was added maintaining T<-65° C. At this temperature stirring was continued for 30 min, then triisopropylborate (17.3 ml, 75 mmol) was added. The reaction mixture was brought to rt and treated with 3N HCl (100 ml). After 15 min the organic phase was dried (Na2SO4), evaporated and precipitated with pentane to provide the title compound (3.83 g, 60%) as a white solid material. MS: m/e=173 (M-H-).

References:

US2003/229096,2003,A1 Location in patent:Page 20

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References

1056246-70-8 Synthesis