ChemicalBook CAS DataBase List 2-(Trifluormethoxy)phenylboronic acid

2-(Trifluormethoxy)phenylboronic acid synthesis

4synthesis methods

Product Name:2-(Trifluormethoxy)phenylboronic acid
CAS Number:175676-65-0
Molecular formula:C7H6BF3O3
Molecular Weight:205.93

64115-88-4 Synthesis

64115-88-4
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175676-65-0
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Yield: 65%

Reaction Conditions:

Stage #1:1-bromo-2-(trifluoromethoxy)benzene with n-butyllithium in tetrahydrofuran at -78; for 0.75 h;
Stage #2: with Triisopropyl borate in tetrahydrofuran at -78 - 20; for 16 h;
Stage #3: with hydrogenchloride;sodium hydroxide;watermore than 3 stages;

Steps:

1.3 EXAMPLE 1; 20 5-METHYL-L-R2&No.x0;-(TRIFLUOROMETHOXY)-L O L&No.x0;-BIPHENYL-3-YLL-LH-PYRAZOLE-3- carboxamide; Step 3: 2-(TRIFLUOROMETHOXY) PHENYLBORONIC ACID
n-Butyllithium (5.9 ml, 9.5 mmol) was added to a solution of 1-BROM-2- (trifluoromethoxy) benzene (2 g, 8.2 mmol) in tetrahydrofuran (28 ML) at-78°C and stirred for 45 minutes. Triisopropyl borate (2. 58 ml, 11.1 mmol) was added dropwise to the reaction mixture and the solution was slowly brought to room temperature over 16 hours. The reaction mixture was quenched with water, made basic with 2N NAOH and extracted with ethyl acetate. The aqueous solution was acidified with 2N HCI, stirred for 1 hour at room temperature and extracted into ethyl acetate. The organic layer was washed with water, brine solution and dried over sodium sulfate. It was filtered and concentrated to give the product (1.10 g, 65%) as a white solid. &No.x0;HNMR (CDCL3) ( 8, ppm): 7.96 (dd, J= 7.2, 1.6 Hz, 1 H), 7.53 (ddd, J = 9.1, 7.3, 1. 8 HZ, 1 H), 7.38 (td, J = 7.3, 0.7 Hz, 1 H), 7.28 (d, J = 8.2 Hz, 1 H), 5.25 (br s, 2H). MS: m/e 206.9 (M+1) +.

References:

MERCK & CO., INC. WO2004/92140, 2004, A1 Location in patent:Page 38