tert-butyl 3-bromo-4-methylbenzoate synthesis

8synthesis methods

Product Name:tert-butyl 3-bromo-4-methylbenzoate
CAS Number:160952-57-8
Molecular formula:C12H15BrO2
Molecular Weight:271.15

7697-26-9 Synthesis

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Yield:160952-57-8 95%

Reaction Conditions:

with trifluorormethanesulfonic acid;sodium hydrogencarbonate

Steps:

66.a a)

a) t-butyl 3-bromo-4-methylbenzoate A mixture of 3-bromo-4-methylbenzoic acid (10.75 g, 50 mmol) in dry ether (50 mL) in a glass bomb was cooled to -30° C. and isobutylene gas was bubbled in to give a total reaction volume of approximately 150 mL. Trifluoromethanesulfonic acid (0.22 g, 2.5 mmol) was added dropwise to the stirred mixture, and the bomb was sealed. The reaction was allowed to warm to RT and was stirred for 6 d. The bomb was opened carefully, and 5% sodium bicarbonate (50 mL) was added slowly. The mixture was allowed to stir for 15 min and ether (250 mL) was added. The layers were separated and the organic layer was washed with 5% sodium bicarbonate (2*50 mL) and then with brine (50 mL). Drying (magnesium sulfate) and concentration gave the title compound (12.88 g, 95%) as a yellow oil. TLC R_f 0.68 (toluene); ¹H NMR (250 MHz, CDCl₃) δ8.13 (d, J=1.7 Hz, 1 H), 7.81 (dd, J=7.9, 1.7 Hz, 1 H), 7.27 (d, J=7.9 Hz, 1 H), 2.44 (s, 3H), 1.59 (s,9 H); IR (CCl₄) 1715, 1368, 1297, 1255, 1170, 1123, 1115 cm^-1; MS(ES) m/e 273.0 [M+H]⁺, 271.0 [M+H]⁺, 214.8 [M+H-C₄H₈]⁺.