Iodine chloride → Methyl 5-iodo-2-methoxy-4-methylbenzoate

Temperature

50 °C

To a solution of methyl 2-methoxy-4-methylbenzoate (2.6 g, 14.43 mmol) in methanol (25 ml) at room temperature in a 100 ml round bottomed (RB) flask was added iodine monochloride (3.62 ml, 72.1 mmol) in methanol dropwise. The reaction mixture was heated at 50° C. for 15 hours. The methanol was concentrated, diluted with water and extracted with ethyl acetate (3×25 ml). The combined organic extracts were washed with 0.1N HCl, water and brine solution. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was used for the next step without further purification (3.2 g, 73%). LCMS: (ES+) m/z=307 (M+H)+; Column: ZORBAX SB C18 (4.6×50) mm, 5 μm; Moblie (M) phase A: 10% MeOH-90% H2O-0.1% TFA; Moblie (M) phase B: 90% MeOH-10% H2O-0.1% TFA; Flow: 5 ml/min; Time (min.): 0 2 3; % B: 0 100 0; Retention Time (RT): 1.87 min.

1. concentrationThe methanol was concentrated
2. additiondiluted with water
3. extractionextracted with ethyl acetate (3×25 ml)
4. washThe combined organic extracts were washed with 0.1N HCl, water and brine solution
5. dry with materialThe organic layer was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude material was used for the next step without further purification (3.2 g, 73%)
9. customRetention Time (RT)
10. custom1.87 min.

ORD record

ord-d31a8901faf243f2952617c723419f12

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09303020B2