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ChemicalBook CAS DataBase List 4-(Methoxymethoxy)bromobenzene

4-(Methoxymethoxy)bromobenzene synthesis

8synthesis methods

Product Name:4-(Methoxymethoxy)bromobenzene
CAS Number:25458-45-1
Molecular formula:C8H9BrO2
Molecular Weight:217.06

106-41-2
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13057-17-5 Synthesis

13057-17-5
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25458-45-1
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Yield: 92%

Reaction Conditions:

Stage #1:4-bromo-phenol with sodium hydride in tetrahydrofuran at 0; for 0.5 h;Inert atmosphere;
Stage #2:bromethyl methyl ether in tetrahydrofuran at 20; for 4 h;Inert atmosphere;

Steps:

5.2.1. Bromo-4-(methoxymethoxy) benzene (7)
To suspension of sodium hydride (0.887 g, 23.12 mmol, 60%dispersion in paraffin oil) in dry THF (30 mL) at 0 °C was slowlyadded a solution of 4-bromophenol (9) (4.0 g, 60.78 mmol) in dryTHF (20 mL) under nitrogen atmosphere and mixture was allowedto stir for 30 min at which point the hydrogen gas evolution hadstopped. The resultant mixture was cooled to 0 C and, bromomethylmethyl ether (27.74 mL, 66.87 mmol) was added dropwiseand stirred for an additional 4 h at rt. After completion of reaction,the reaction mixturewas quenched with Ice-cold water and extractwith Ethyl acetate and the organic layerwaswashed with brine anddried over Na2SO4. The solvent was removed under reduced pressure,and the crude product was subjected to flash column chromatography(5% ethyl acetate-hexane) to give compound 7 (4.61 gr,92%) as colour less oil; IR (neat): 2956, 2902, 2826,1590,1487,1233,1152, 997, 824 cm1; 1H NMR (600 MHz, CDCl3) δ 7.38 (d, J 9.0 Hz,1H), 6.93 (d, J 9.0 Hz, 1H), 5.14 (s, 1H), 3.47 (s, 2H); 13C NMR(150 MHz, CDCl3) d 156.13, 132.12 (2 C), 117.88 (2 C), 114.01, 94.30,55.85 ppm; ESI-MS: m/z 217 [M].

References:

Venkanna, Arramshetti;Cho, Kyo Hee;Dhorma, Lama Prema;Kumar, Duddukuri Nandan;Hah, Jung Mi;Park, Hyeung-geun;Kim, Sun Yeou;Kim, Mi-hyun [European Journal of Medicinal Chemistry,2019,vol. 163,p. 453 - 480]

106-41-2
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$13.00/5g