ChemicalBook CAS DataBase List 3-ETHYNYL-BENZOIC ACID METHYL ESTER

3-ETHYNYL-BENZOIC ACID METHYL ESTER synthesis

10synthesis methods

Product Name:3-ETHYNYL-BENZOIC ACID METHYL ESTER
CAS Number:10602-06-9
Molecular formula:C10H8O2
Molecular Weight:160.17

67-56-1 Synthesis

67-56-1
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914943-91-2 Synthesis

914943-91-2
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10602-06-9
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$15.00/100mg

Yield: 96%

Reaction Conditions:

Stage #1:tert-butyl 3-ethynylbenzoate with trifluoroacetic acid in dichloromethane at 20; for 3 h;
Stage #2:methanol with sulfuric acid at 65; for 20 h;

Steps:

7.a Methyl 3-ethynylbenzoate (131)
terf-Butyl 3-ethynylbenzoate (117) (1.50 g, 9.37 mmoi) was dissolved in dry DCM (70 mL) and TFA (35.9 mL, 488 mmoi) was added carefully. The reaction was stirred at room temperature for 3 hours, concentrated in vacuo and toluene was added and then removed in vacuo to give a pale yellow solid. This material was dissolved in methanol (50 mL) and cone. H₂S0₄ (-1 mL) was added and the resulting solution was stirred at 85 °C for 20 hours. Upon cooling to room temperature, the volatiies were removed in vacuo and the residue was diluted with EtOAc (200 mL) and sat. aq. NaHCO₃ (100 mL) was added slowly. The layers were separated and the aqueous layer was extracted with EtOAc (200 mL), the organic layers were combined and washed with water (100 mL), brine (100 mL), dried ( gS0₄), filtered and concentrated in vacuo to give the title compound (131) (1.136 g, 96% yield over 2 steps) as a pale yellow solid; ¹H NMR (400 MHz, CDCI₃) δ 8.17 (t, J = 1.5 Hz, 1 H), 8.03 - 8.00 (m, 1 H), 7.66 (dt, J = 7.7, 1.4 Hz, 1 H), 7.41 (td, J = 7.8, 0.4 Hz, 1 H), 3.93 (s, 3H), 3.12 (s, 1 H). LCMS Method C: rt 5.84 min.

References:

CANCER THERAPEUTICS CRC PTY LTD;DEVLIN, Mark Graeme;STREET, Ian Philip;TONG, Warwick Bonner WO2014/27199, 2014, A1 Location in patent:Page/Page column 75

77123-59-2 Synthesis