3-(3-Iodophenyl)propionic acid → Benzenepropanol, 3-iodo-

Temperature

0 °C

To an ice cooled solution of 3-(3-iodophenyl)propionic acid (8.0 g, 29.7 mmol) in THF (30 mL) was added 1.0 M BH3 in THF (40 mL, 40 mmol). The mixture was stirred at 0° C. for 1 hour, then quenched by careful addition of 1:1 THF:H2O (10 mL). The mixture was concentrated in vacuo, the residue taken up in diethyl ether (100 mL), washed with water (1×100 mL, 1×50 mL), and brine (1×25 mL), dried over MgSO4, filtered, and concentrated to an oil. The oil was purified via silica gel chromatography, eluting with 40% ethyl acetate in hexanes to provide the titled compound (6.3 g, 81%). 1H NMR (300 MHz, d6-DMSO) δ 7.58 (d, 1H, J=1.4 Hz), 7.53 (ddd, 1H J=1.0, 1.7, 6.1 Hz), 7.22 (dd, 1H, J=1.7, 6.4 Hz), 7.08 (t, 1H, J=7.6 Hz), 4.47 (t, 1H, J=5.1 Hz), 3.38 (dt, 2H, J=5.1, 6.3 Hz), 2.57 (t, 2H, J=7.8 Hz), 1.68 (m, 2H); MS (ESI) m/z 279 (M+NH4).

1. customquenched by careful addition of 1:1 THF
2. concentrationThe mixture was concentrated in vacuo
3. washwashed with water (1×100 mL, 1×50 mL), and brine (1×25 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated to an oil
7. customThe oil was purified via silica gel chromatography
8. washeluting with 40% ethyl acetate in hexanes

ORD record

ord-d07c0e87cac0486eb2a6728e5603dd33

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07169797B2