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ChemicalBook CAS DataBase List 4-(2-Methoxyphenyl)phenylboronic acid
1107041-07-5

4-(2-Methoxyphenyl)phenylboronic acid synthesis

3synthesis methods
-

Yield:1107041-07-5 80%

Reaction Conditions:

Stage #1: 4’-bromo-2-methoxy-1,1'-biphenylwith n-butyllithium in tetrahydrofuran at -40; for 1 h;
Stage #2: with Triisopropyl borate in tetrahydrofuran at -40 - 0; for 2 h;

Steps:

Intermediate 2b: (2’-Methoxybiphenyl-4-yl)boronic acid

To a stirred solution of 4’-Bromo-2-methoxybiphenyl (7.0 g, 26.6 mmol) in dry THE(70 mL) at -40 00 n-BuLi (12.8 mL) was added and maintained at -40 00 for 1 h. Tothe above solution, triisproprylborate (10.01 g, 53.2 mmol) was added drop wise at - 40 00 and temperature was raised to 0 00 over a period for 2 h. The reaction mixture was quenched with saturated A1013 solution and NaOH solution. It was washed with ether and acidified with 1 N HCI solution, extracted with ethyl acetate, with water andbrine solution. The solvent was dried over anhydrous Na2SO4, removed under vacuo and washed with n-hexane to yield the title product (4.8 g, 80.0%) as a brown solid.LOMS: (M-H) =227.0

References:

WO2014/202580,2014,A1 Location in patent:Page/Page column 72