4-Bromo-2-chlorobenzonitrile → (4-Bromo-2-chlorophenyl)methanamine

Temperature

23 °C

To a solution of 4-bromo-2-chlorobenzonitrile (2500 mg, 11549 μmol) in THF (20 mL) at 0° C. was added borane-methyl sulfide complex, 2.0 m sol in THF (28873 μl, 57747 μmol). Ice bath removed and reaction stirred overnight warming to 23° C. Reaction cooled to 0° C. and quenched with MeOH (15 mL). Reaction then partitioned between CHCl3 (100 mL) and 1M NaOH (100 mL). Organic dried with brine and MgSO4. Organic then concentrated to an oil under reduced pressure and purified on silica (80 g) eluting with 0>6% 2M NH3 in MeOH/DCM and product isolated as a colorless oil. MS (ESI pos. ion) m/z: 220/222 (MH+). Calc'd exact mass for C7H7BrClN: 219/221

1. customIce bath removed
2. customreaction
3. customReaction
4. temperaturecooled to 0° C.
5. customquenched with MeOH (15 mL)
6. customReaction
7. customthen partitioned between CHCl3 (100 mL) and 1M NaOH (100 mL)
8. dry with materialOrganic dried with brine and MgSO4
9. concentrationOrganic then concentrated to an oil under reduced pressure
10. custompurified on silica (80 g)
11. washeluting with 0>6% 2M NH3 in MeOH/DCM and product
12. customisolated as a colorless oil

ORD record

ord-253495461d894022a97902c47499aa45

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08198448B2