ChemicalBook CAS DataBase List 4-Bromo-2,6-di-tert-butylanisole

4-Bromo-2,6-di-tert-butylanisole synthesis

6synthesis methods

Product Name:4-Bromo-2,6-di-tert-butylanisole
CAS Number:1516-96-7
Molecular formula:C15H23BrO
Molecular Weight:299.25

1516-95-6 Synthesis

Benzene, 1,3-bis(1,1-dimethylethyl)-2-methoxy-

1516-95-6
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Benzenemethanol, α-ethynyl-α-phenyl-, 1-acetate

3848-49-5
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Yield:3848-49-5 96%

Reaction Conditions:

with NBS in acetonitrile; for 20 h;

Steps:

7 5-bromo-l,3-di-tert-butyl-2-methoxybenzene

l,3-di-tert-butyl-2-methoxybenzene (Bai, Xinyan et al, Tetrahedron, 69(3), 1105-1111; 2013 (2.0 g, 9.1 mmol) was dissolved in acetonitrile (30.0 mL) and treated with n-bromosuccinimide (1.7 g, 9.5 mmol) and the mixture allowed to stir for 20 hours. The mixture was concentrated in vacuo then filtered through a Si02 plug with hexanes. The solvent was then removed in vacuo to provide an oil (2.6g, 96%) used without further purification. 1H NMR (500 MHz, Chloroform-d) d 7.34 (s, 2H), 3.68 (s, 3H), 1.41 (s, 18H).

References:

WO2020/150668,2020,A1 Location in patent:Paragraph 0191