Dimethyl Sulfide → (5-Bromo-2-iodophenyl)methanol

Temperature

65 °C

To a stirred mixture of acid 2-iodo-5-bromobenzoic acid (15.0 g, 45.9 mmol) in dry THF (100 mL) under argon was added neat BH3.DMS (16.0 mL, 169 mmol) dropwise over 20 minutes. The resulting mixture was heated at 65° C. for 8 hours, cooled to room temperature and quenched by the dropwise addition of water (40 mL). The reaction mixture was concentrated in vacuo. The crude alcohol was diluted with of EtOAc (300 mL), washed with 1N NaOH (2×30 mL), 1N HCl (1×30 mL), saturated aqueous NaHCO3 solution (1×30 mL) and brine (1×30 mL). The EtOAc layer was dried (MgSO4), filtered and concentrated in vacuo to give 2-iodo-5-bromobenzyl alcohol (13.8 g, 96%). 1H NMR (CDCl3): δ 7.56 (d, 1H, J=8.25 Hz), 7.54 (s, 1H), 7.04 (d, 1H, J=8.25 Hz), 4.47 (s, 2H). HPLC: Rt=3.12 min. m/z=312 (M+H+).

1. additionwas added neat BH3
2. temperaturecooled to room temperature
3. customquenched by the dropwise addition of water (40 mL)
4. concentrationThe reaction mixture was concentrated in vacuo
5. additionThe crude alcohol was diluted with of EtOAc (300 mL)
6. washwashed with 1N NaOH (2×30 mL), 1N HCl (1×30 mL), saturated aqueous NaHCO3 solution (1×30 mL) and brine (1×30 mL)
7. dry with materialThe EtOAc layer was dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-db0ed4ef06ef44a6baa27e26b7f740d9

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07417040B2