2-(4-CHLORO-3-METHYLBENZOYL)BENZOIC ACID synthesis

9synthesis methods

Product Name:2-(4-CHLORO-3-METHYLBENZOYL)BENZOIC ACID
CAS Number:141123-11-7
Molecular formula:C15H11ClO3
Molecular Weight:274.7

85-44-9 Synthesis

85-44-9
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$9.00/5g

54932-72-8 Synthesis

54932-72-8
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$6.00/1g

2-(4-CHLORO-3-METHYLBENZOYL)BENZOIC ACID

141123-11-7
14 suppliers
$387.00/1g

Yield:141123-11-7 50.4%

Reaction Conditions:

Stage #1: 2-chloro-5-bromotoluenewith n-butyllithium in tetrahydrofuran at -78; for 0.5 h;
Stage #2: phthalic anhydride in tetrahydrofuran at -78; for 2 h;

Steps:

To a stirring solution of 4-bromo-1-chloro-2-methyl-benzene 5 (4.92mL, 37.1mmol) in THF (75mL) cooled to -78°C was added n-butyllithium (14.9mL, 37.1mmol) dropwise. The solution was stirred at -78°C for 30min and then was added to a stirring solution of phthalic anhydride 6 (5.00g, 33.8mmol) in THF (90mL) at -78°C. The reaction was stirred at -78°C for 2h before being quenched with 1N HCl (100mL). The solution was allowed to warm to rt, the layers were separated and the aqueous layer was extracted with EtOAc (3×100mL). The combined organic layers were passed through a phase separator and concentrated. The crude material was purified using Teledyne ISCO Combi-Flash system (solid loading, 40G column, 40-80% EtOAc, 20min run) to give 2-(4-chloro-3-methyl-benzoyl)benzoic acid 7 (4.67g, 50.4% yield) as a white solid. ¹H NMR (400MHz, CDCl₃) δ (ppm): 8.10 (d, J=7.8Hz, 1H), 7.68 (dt, J=7.6, 1.2Hz, 1H), 7.64-7.62 (m, 1H), 7.59 (dt, J=7.9, 1.2Hz, 1H), 7.44 (dd, J=8.2, 2.2Hz, 1H), 7

References:

McGowan, Kevin M.;Nance, Kellie D.;Cho, Hykeyung P.;Bridges, Thomas M.;Jeffrey Conn;Jones, Carrie K.;Lindsley, Craig W. [Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,# 6,p. 1356 - 1359]

85-44-9 Synthesis

85-44-9
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$9.00/5g

95-49-8 Synthesis