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ChemicalBook CAS DataBase List 6-(bromomethyl)-2,3-dihydrobenzo[b][1,4]dioxine

6-(bromomethyl)-2,3-dihydrobenzo[b][1,4]dioxine synthesis

4synthesis methods
-

Yield:79440-34-9 84%

Reaction Conditions:

with phosphorus tribromide in dichloromethane at 0; for 0.5 h;

Steps:

6-(bromomethyl)-2,3-dihydrobenzo[b][l,4]dioxine (116).

To a solution of (2,3- dihydrobenzo[b][l,4]dioxin-6-yl)methanol (2.77 g, 16.66 mmol) in CH2CI2 was added PBn (0.63 mL, 6.66 mmol) dropwise at 0 °C. The mixture was stirred at 0 °C for 0.5 h. Upon completion, the mixture was diluted with CH2CI2 and washed with saturated NaHCCL. The organic layer was concentrated under vacuum. Colorless oil (hexanes :ethyl acetate = 20:1, 3.22 g, 84% yield) was isolated with column chromatography. 1 H NMR (500 MHz, Chlorol'ornw/) d 6.92 (d, J = 3.1 Hz, 1H), 6.88 (dd, J = 8.4, 2.5 Hz, 1H), 6.82 (dt, J = 8.4, 2.4 Hz, 1H), 4.44 (d, J = 2.0 Hz, 2H), 4.28 - 4.21 (m, 4H). 13C NMR (126 MHz, Chloroform-^/) d 143.82, 143.46, 130.93, 122.28, 118.02, 117.55, 64.39, 64.27, 33.82

References:

WO2019/191410,2019,A1 Location in patent:Page/Page column 40

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