2-Iodobenzyl alcohol

white to yellow or pinkish needle-like powder

To a THF solution (16 mL) of commercially available o-iodobenzoicacid (4.15 g, 16.8 mmol) was added boran–dimethylsulfide complex (1.90 mL, 20.0 mmol) at 0°C. After stirring for 15 h at room temperature, phosphate buffer (pH 7) was added. Organic materials were extracted with ethyl acetate three times. The combined extracts were washed with brine and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, o-iodobenzylalcohol (3.84 g, 98 percent) was obtained as a white solid and used for the next step without further purification. To a DCM suspension (33 mL) of manganese(IV) oxide (14.0 g, 161 mmol) was added the crude o-iodobenzylalcohol (3.77 g, 16.1 mmol). After stirring for 30 h at room temperature, the resulting suspension was filtrated through a small pad of celite using DCM as an eluent. After removal of the solvent under reduced pressure, the residue was purified by column chromatography on silica gel (hexane/ethyl acetate 5:1) to give o-iodobenzaldehyde (3.36 g, 90percent) as pale yellow crystals.To a solution of 2-iodobenzoic acid (5.3 g, 21 mmol) in tetrahydrofuran (43 mL) at 0 °C, was addedborane-dimethyl sulfide (2.2 mL, 24 mmol) dropwise over 20 minutes. The reaction mixture wasstirred vigorously at room temperature for 16 hours then quenched with methanol (1 mL) followed bya saturated aqueous solution of potassium carbonate (5 mL). The layers were separated and theaqueous layer extracted with ethyl acetate (2 × 20 mL). The combined organic layers were washedwith water (10 mL) and saturated aqueous sodium chloride (20 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was recrystallised from hexanes affording(2-iodophenyl)methanol S1 (4.7 g, 94percent) as long white crystals; mp 90–92 °C (lit., 1 90–95 °C); Rf =0.82 (1:1 hexanes-ethyl acetate); δH (400 MHz; CDCl3) 7.82 (1H, d, J = 7.6 Hz, ArH), 7.46 (1H, dd, J= 7.6, 1.5 Hz, ArH), 7.40 (1H, t, J = 7.6 Hz, ArH), 7.00 (1H, dt, J = 7.6, 1.5 Hz, ArH), 4.68 (2H, d, J = 6.2 Hz, CH2), 2.00 (1H, t, J = 6.2 Hz, OH); The spectroscopic data were in agreement with thatreported in the literature.

Molecular Weight:234.03
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:233.95416
Monoisotopic Mass:233.95416
Topological Polar Surface Area:20.2
Heavy Atom Count:9
Complexity:85
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes