Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9]Br.[Na+].[I-].[C:13]([S-:15])#[N:14].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][N:14]=[C:13]=[S:15]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 1-bromo-2-(bromomethyl)-4-fluorobenzene (12, 5.36 g, 20.0 mmol) in dry DMF (20 mL) was added NaI (1.20 g, 8.00 mmol) and KSCN (3.88 g, 40.0 mmol). The mixture was heated under N2 at 80° C. for 12 h. After cooling to RT, the mixture was diluted with water (100 mL), and extracted with EtOAc (50 mL×2). The combined extracts were washed with brine, dried over MgSO4 and concentrated to give crude product. This was purified by column chromatography on silica gel, and eluted with petroleum ether to provide 1-bromo-4-fluoro-2-(isothiocyanatomethyl)benzene (13).
Workup
- temperatureAfter cooling to RT
- extractionextracted with EtOAc (50 mL×2)
- washThe combined extracts were washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated
- customto give crude product
- customThis was purified by column chromatography on silica gel
- washeluted with petroleum ether
Sources & evidence
- ORD record
- ord-5dcaa496b0594bcb9620f803335dbacb
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08648073B2
Linked notes
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