Sulfuric Acid → 3-Iodo-2-naphthalenemethanol

Temperature

0 °C

A solution of (3-amino-2-naphthyl)methanol (500 mg, 2.89 mmol) in water (3 mL), acetone (3 mL) and concentrated HCl (1.6 mL) was cooled to 0° C. and a solution of sodium nitrite (219 mg, 3.18 mmol) in water (0.7 mL) was added. The reaction was stirred for 2 h at 0° C. and a solution of potassium iodide (719 mg, 4.33 mmol) and concentrated H2SO4 (0.16 mL) in water (1.2 mL) was added. The reaction mixture was heated at 60° C. for 2-3 h. The reaction mixture was cooled to room temperature and 50% saturated Na2SO3 (30 mL) was added. The mixture was extracted with CH2Cl2 (3×20 mL) and the combined extracts were washed with brine (20 mL), dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 25×160 mm, 0-40% EtOAc in hexanes gradient) to afford (3-iodo-2-naphthyl)methanol. Rf=0.47 (20% EtOAc/hexanes). 1H NMR (600 MHz, CD3OD): δ 8.35 (s, 1H); 7.91 (s, 1H); 7.81 (d, J=8.0 Hz, 1H); 7.71 (d, J=8.0 Hz, 1H); 7.47-7.42 (m, 2H); 4.69 (s, 2H).

1. temperatureThe reaction mixture was heated at 60° C. for 2-3 h
2. temperatureThe reaction mixture was cooled to room temperature
3. extractionThe mixture was extracted with CH2Cl2 (3×20 mL)
4. washthe combined extracts were washed with brine (20 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated in vacuo
7. customto give the crude product
8. customThis was purified by flash chromatography (Si, 25×160 mm, 0-40% EtOAc in hexanes gradient)

ORD record

ord-f5f7cc78c6124da8a1151e8529a66a3d

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07910592B2