Uses
2-Iodobenzyl alcohol was used in the synthesis of substituted seven-membered lactones, 2-[(E)-(1?-iodo-2?-propenyl)]benzyl alcohol2 and 2,3-diphenyl-1-indenone.
Synthesis
The general procedure for the synthesis of 2-iodobenzyl alcohol from 2-iodobenzoic acid was as follows: to a tetrahydrofuran (THF) solution (16 mL) of commercially available o-iodobenzoic acid (4.15 g, 16.8 mmol) was slowly added borane-dimethyl sulfide complex (1.90 mL, 20.0 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 15 hours before the reaction was quenched by the addition of phosphate buffer (pH 7). Subsequently, the reaction mixture was extracted three times with ethyl acetate and the organic phases were combined. The organic phase was washed with saturated brine and dried with anhydrous sodium sulfate. Concentration under reduced pressure to remove the solvent gave o-iodobenzyl alcohol (3.84 g, 98% yield) as a white solid, which could be used in the next reaction without further purification. The crude o-iodobenzyl alcohol (3.77 g, 16.1 mmol) was added to a dichloromethane (DCM, 33 mL) suspension of dimethyl sulfoxide (DMSO, 14.0 g, 161 mmol). The reaction mixture was stirred at room temperature for 30 h before being filtered through a diatomaceous earth pad, using dichloromethane as the eluent. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 5:1) to afford o-iodobenzaldehyde (3.36 g, 90% yield) as light yellow crystals.
References
[1] Chemistry - A European Journal, 2018, vol. 24, # 70, p. 18653 - 18657
[2] Tetrahedron Letters, 1987, vol. 28, # 2, p. 171 - 174
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 15, p. 4669 - 4678
[4] Organic Letters, 2015, vol. 17, # 5, p. 1126 - 1129
[5] Journal of Fluorine Chemistry, 2015, vol. 179, p. 106 - 115
