Methyl 4-Acetyl-2-fluorobenzoate synthesis

2synthesis methods

Product Name:Methyl 4-Acetyl-2-fluorobenzoate
CAS Number:1006876-12-5
Molecular formula:C10H9FO3
Molecular Weight:196.18

67-56-1 Synthesis

67-56-1
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1029714-95-1 Synthesis

1029714-95-1
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1006876-12-5
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Yield:1006876-12-5 62.4%

Reaction Conditions:

Stage #1: 4-acetyl-2-fluorobenzoic acidwith oxalyl dichloride;N,N-dimethyl-formamide in dichloromethane at 0 - 20; for 3 h;
Stage #2: methanolwith triethylamine in dichloromethane at 0 - 20; for 1 h;

Steps:

13.5

4-Acetyl-2-fluorobenzoic acid (46.1 mmol, 0.0461 mol) in dichloromethane (30 mL) was treated with oxalyl chloride (7.8 mL, 92 mmol) and N,N-dimethylformamide (0.2 mL) at 0 ⁰C. The reaction mixture was stirred at ambient temperature for 3 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane (50 mL, 0.78 mol) and cooled to 0 ⁰C. A solution of methanol (4.7 mL) and triethylamine (16 mL, 120 mmol) was added. The reaction mixture was stirred at ambient temperature for 1 h, washed with water aqueous IN hydrochloric acid, and brine. The organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with 20% ethyl acetate in hexanes to afford the desired product. (5.64 g, 62.4%).

References:

WO2008/64157,2008,A1 Location in patent:Page/Page column 49-50

111-34-2 Synthesis

111-34-2
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179232-29-2 Synthesis

179232-29-2
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1006876-12-5
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References