1-BroMo-3-cyclobutoxy-benzene synthesis

Yield:1268713-64-9 91%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 120; for 6 h;

Steps:

1 Step 1:

A mixture of 3-bromophenol (1.00 g, 5.78 mmol, 1.00 eq.), bromocyclobutane (1.17 g, 8.65 mmol, 0.82 mL, 1.50 eq.) and potassium carbonate (3.20 g, 23.1 mmol, 4.00 eq.) in DMF (10 mL) and stirred at 120° C. for 6 hours. The reaction mixture was diluted with water (80 mL) and extracted with (petroleum ether/ethyl acetate 20%) (50 mL×3) and the combined extracts were washed with aqueous sodium hydroxide (1.00 M, 50 mL), brine (50 mL) and dried over sodium sulfate and concentrated to give 1-bromo-3-(cyclobutoxy)benzene (1.20 g, 5.27 mmol, 91% yield) as a colorless oil. ¹H NMR (400 MHz, CDCl₃) δ=7.04-6.93 (m, 2H), 6.86 (t, J=2.4 Hz, 1H), 6.64 (ddd, J=1.2, 2.4, 8.0 Hz, 1H), 4.60-4.44 (m, 1H), 2.34 (tddd, J=2.8, 6.8, 8.0, 9.6 Hz, 2H), 2.14-1.98 (m, 2H), 1.83-1.71 (m, 1H), 1.66-1.50 (m, 1H).

References:

US2021/78994,2021,A1 Location in patent:Paragraph 0315