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ChemicalBook CAS DataBase List 6-BROMO-2,3-DIHYDRO-1H-INDENE-1-CARBOXYLIC ACID
52651-16-8

6-BROMO-2,3-DIHYDRO-1H-INDENE-1-CARBOXYLIC ACID synthesis

3synthesis methods
783335-58-0 Synthesis
6-BROMO-2,3-DIHYDRO-1H-INDENE-1-CARBONITRILE

783335-58-0
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Yield:52651-16-8 100 %

Reaction Conditions:

with potassium hydroxide in ethanol at 100;

Steps:

96.1

To a solution of 6-bromo-2,3-dihydro-1 H-indene-1-carbonitrile (1 g, 4.50 mmol) in EtOH (60 mL) was added KOH (20 g, 178.24 mmol, 20 mL , 50% purity), the mixture was stirred at 100 °C for 16 hrs. The mixture was concentrated to give a solution, the solution was extracted with MTBE (100 mL) , the aqueous phase was adjusted to pH=3 with 1 N HCI, the solution was extracted with EA (100 mL *3), the combined organic layer was washed with brine (200 mL) , dried over Na2SO4, filtered and concentrated to give Intermediate B (1.09 g, 100% yield,) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ = 13.12 - 11 .89 (m, 1 H), 7.48 (s, 1 H), 7.38 - 7.35 (m, 1 H), 7.21 (d, J = 8.0 Hz, 1 H), 4.03 - 3.99 (m, 1 H), 2.91 - 2.79 (m, 2H), 2.28 - 2.22 (m, 2H) ppm.

References:

WO2021/155316,2021,A1 Location in patent:Page/Page column 224-225