Cyanogen Bromide → HCID 59323784, compound

To a stirred, cooled (0° C.) solution of (RS)-2-amino-2-(4-bromo-3-fluoro-phenyl)-ethanol (3.26 g) and sodium acetate (2.22 g) in methanol (25 ml) was added dropwise a solution of cyanogen bromide (1.52 g) in methanol (10 ml) over 10 min. The mixture was then allowed to warm to at r.t. and stirring continued for 16 h. The mixture was concentrated in vacuo and the residue was resuspended in water and made basic by addition of 1 M aq sodium hydroxide solution. The mixture was then extracted twice with dichloromethane and the combined organic phases were dried over sodium sulphate and concentrated in vacuo. The residue was triturated in dichloromethane and the resultign crystals washed with ether to give (RS)-4-(4-bromo-3-fluoro-phenyl)-4,5-dihydro-oxazol-2-ylamine (1.09 g, 30%) as a white solid. MS (ISP): 261.0 ([{81Br}M+H]+), 258.9 ([{79Br}M+H]+).

1. concentrationThe mixture was concentrated in vacuo
2. additionmade basic by addition of 1 M aq sodium hydroxide solution
3. extractionThe mixture was then extracted twice with dichloromethane
4. dry with materialthe combined organic phases were dried over sodium sulphate
5. concentrationconcentrated in vacuo
6. customThe residue was triturated in dichloromethane
7. washthe resultign crystals washed with ether

ORD record

ord-0a2e66071b6e4fac9e988854ce38076f

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604061B2