Oxalyl chloride → (2-Bromo-5-iodo-phenyl)-chroman-6-yl-methanone

To a stirred solution of 2-bromo-5-iodobenzoic acid (1.0 g, 3.06 mmol) in DCM (5 mL) was added DMF (0.2 mL) and oxalyl chloride (0.44 mL, 4.59 mmol) at 0° C. After complete addition, the reaction mixture was stirred at room temperature for 3 h. The volatiles were evaporated under reduced pressure, and the crude product was dissolved in DCM (4 mL) and added to chroman (488 mg, 3.67 mmol) which had been cooled to 0° C. To this mixture was added aluminum chloride (488 mg, 3.67 mmol) in portions. After stirring for 4 h, the reaction was quenched by pouring it into crushed ice. This was extracted with dichloromethane (50 mL×2). The dichloromethane layers were combined and washed with water (20 mL), saturated aqueous sodium bicarbonate solution (20 mL×2), and brine (20 mL), then dried over sodium sulfate, and concentrated. The crude product was purified by column chromatography to furnish (2-bromo-5-iodo-phenyl)-chroman-6-yl-methanone (1.2 g).

1. additionAfter complete addition
2. customThe volatiles were evaporated under reduced pressure
3. dissolutionthe crude product was dissolved in DCM (4 mL)
4. temperaturehad been cooled to 0° C
5. stirringAfter stirring for 4 h
6. customthe reaction was quenched
7. additionby pouring it
8. custominto crushed ice
9. extractionThis was extracted with dichloromethane (50 mL×2)
10. washwashed with water (20 mL), saturated aqueous sodium bicarbonate solution (20 mL×2), and brine (20 mL)
11. dry with materialdried over sodium sulfate
12. concentrationconcentrated
13. customThe crude product was purified by column chromatography

ORD record

ord-8ab0cf2821234239adecb0e80d871d50

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828951B2