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ChemicalBook CAS DataBase List Methyl 4-bromo-2-fluorobenzoate
179232-29-2

Methyl 4-bromo-2-fluorobenzoate synthesis

5synthesis methods
112704-79-7 Synthesis
4-Bromo-2-fluorobenzoic acid

112704-79-7
538 suppliers
$15.00/5 g

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Yield:179232-29-2 100%

Reaction Conditions:

in tetrahydrofuran;methanol;hexanes at 0 - 20; for 1 h;

Steps:

45.1
STEP 1 : To a solution of 4-bromo-2-fluorobenzoic acid (2.0 g, 9.1 mmol) in THF (24 mL) and methanol (6 mL) at 0 °C was added a solution of (trimethylsilyl)diazomethane in hexanes (2.0 M, 5.46 mL, 10.9 mmol). The yellow solution was allowed to gradually warm to room temperature over 1 h. The volatile materials were removed and the residue was treated with aqueous hydrochloric acid (1 M). The aqueous mixture was extracted with ethyl acetate. The organic extract was dried over magnesium sulfate, filtered, and concentrated to provide crude methyl 4- bromo-2-fluorobenzoate (2.7 g, quantitative yield). This material was used in the subsequent step without further purification. 1H NMR (400 MHz, CDCl3): 7.85-7.81 (m, IH), 7.38-7.33 (m, 2H), 3.93 (s, 3H); MS (EI) for C8H6BrFO2: 232, 234 (MH+).

References:

EXELIXIS, INC. WO2009/55077, 2009, A1 Location in patent:Page/Page column 447

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