Methyl 2-iodobenzoate

Chemical Properties

Uses

• N-substituted 4-methylene-3,4-dihydro-1(2H)-isoquinolin-1-ones
• methyl diphenylacetylene-2-carboxylate
• methyl 2-heptynylphenylbenzoate
• (E)-2-[3-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-oxopropyl]benzoic acid methyl ester
• 4-(2-carbomethoxyphenyl)-3-(1-methylethoxy)cyclobut-3-ene-1,2-dione
• 3-(2-carbomethoxyphenyl)-4-methylcyclobuten-3-ene-1,2-dione 2-(ethylene acetal)

Synthesis Reference(s)

General Description

Synthesis

67-56-1

88-67-5

610-97-9

To a 200 mL methanol solution of 2-iodobenzoic acid (15 g, 60 mmol) was slowly added 8.8 mL of concentrated sulfuric acid dropwise. The reaction mixture was heated to reflux for 16 hours. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated by rotary evaporator to about 20 mL. Subsequently, the concentrate was partitioned between water (appropriate amount) and dichloromethane (appropriate amount). The aqueous phase was further extracted with dichloromethane (2 × 150 mL). The organic layers were combined and washed sequentially with saturated sodium bicarbonate solution (3 × 100 mL) and water (3 × 100 mL). The organic layers were dried over anhydrous sodium sulfate, filtered and the solvent was evaporated to give methyl 2-iodobenzoate (47) as a light yellow oil (15.4 g, 98% yield).The infrared spectrum of methyl 2-iodobenzoate (47) (KBr, νmax, cm1): 3444, 3057, 2994, 2946, 2894, 2836, 1728, 1579, 1459, 1428, 1290. 1459, 1428, 1290, 1249, 1127, 1100, 1013, 738.

References