4-Toluenesulfonyl chloride → HCID 20453360, compound

3-(3-Bromophenyl)propane-1-ol (0.59 g), triethylamine (0.57 mL) and 4-dimethylaminopyridine (0.03 g) were dissolved in dichloromethane (6.8 mL), p-toluenesulfonyl chloride (0.62 g) was added, and the resulting mixture was stirred at room temperature for 15 hours. The reaction mixture was partitioned between ethyl acetate (35 mL) and 10% aqueous citric acid (10 mL) The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved in dimethylsulfoxide (9.1 mL), sodium cyanide (0.17 g) was added, and the resulting mixture was stirred at 50° C. for 24 hours. The reaction mixture was partitioned between ethyl acetate (55 mL) and water (30 mL) The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (0.59 g).

1. customThe reaction mixture was partitioned between ethyl acetate (35 mL) and 10% aqueous citric acid (10 mL) The organic layer
2. washwas washed with brine (10 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated under reduced pressure
5. dissolutionThe residue was dissolved in dimethylsulfoxide (9.1 mL)
6. additionsodium cyanide (0.17 g) was added
7. stirringthe resulting mixture was stirred at 50° C. for 24 hours
8. customThe reaction mixture was partitioned between ethyl acetate (55 mL) and water (30 mL) The organic layer
9. washwas washed with brine (10 mL)
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated under reduced pressure

ORD record

ord-391b4680d9684a2a974c6ab212f41510

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07795236B2