4-Iodobenzoic acid → HCID 14054779, compound

Participants

Reaction Conditions

Reaction Steps

(Andersen, K. E.; Mane, R. B.; Desai, U. V.; Hebbalkar, G. D. Collection Czechoslovak Chem. Commun. 1988, 53, 646-657.) 4-Iodobenzoic acid 3 (5.00 g, 19.1 mmol) is dissolved in anhydrous THF (60 ml), the solution is cooled to an internal temperature of −30° C. in a bath of iso-propanol/dry-ice, and i-PrMgCl (2 M in THF; 10.5 ml, 21.0 mmol) is slowly added dropwise, in order to keep the internal temperature at between −20° C. and −30° C. After the reaction mixture is stirred for an additional 40 min at a temperature of −25° C., a solution of 4-formylbenzoic acid methylester (16; 4.07 g, 24.8 mmol) in anhydrous THF (25 ml) is added dropwise, in order to keep the internal temperature at below −20° C. The mixture is stirred for an additional 30 min at −25° C. and is thawed over night to RT. Subsequently, methanol (30 ml) is added, the mixture is poured into water (500 ml), and extracted with Et2O. The organic phases are unified, washed with a saturated solution of NaCl, and dried over MgSO4. The solvent is removed, and the crude product as obtained is crystallized from chloroform/petroleum ether, in order to obtain 4.05 g (71%) of compound 5 as a colorless solid. Melting point 116° C. (Andersen, K. E.; Mane, R. B.; Desai, U. V.; Hebbalkar, G. D. Collection Czechoslovak Chem. Commun. 1988, 53, 646-657.) 123° C.). The spectroscopic data of the isolated compound 5 correspond to the values as published (Andersen et al. 1988, see above).

Provenance & Evidence