Toluene → 2-(3-Bromophenyl)-2-methylbutan-1-amine

A solution of 2-(3-bromophenyl)-2-methylbutanenitrile (1678.5 mg, 7.049 mmol) in dry THF (28 mL) was cooled in an ice-bath. AlH3:(Me)2EtN complex, 0.5M in PhMe (28.20 mL of 0.5 M, 14.10 mmol) was added slowly dropwise and the resultant solution stirred at 0° C. for 30 mins. The mixture was allowed to warm to RT and stirred for 4.5 hours. The reaction was carefully quenched by dropwise addition of 1:1 THF:water (˜30 mL). The resulting suspension was stirred vigorously and filtered through a pad of celite. The collected solid was partitioned between EtOAc and brine and the aqueous layer further extracted with EtOAc (3×50 mL) and the combined organics dried over Na2SO4, filtered and concentrated under reduced pressure to give a light brown oil. The residue was purified on silica gel by flash column chromatography (5% MeOH in DCM, loaded in DCM, ˜200 mL silica) to give the product as a yellow oil (1137.8 mg, 67% Yield).

1. customThe reaction was carefully quenched by dropwise addition of 1:1 THF
2. stirringThe resulting suspension was stirred vigorously
3. filtrationfiltered through a pad of celite
4. customThe collected solid was partitioned between EtOAc and brine
5. extractionthe aqueous layer further extracted with EtOAc (3×50 mL)
6. dry with materialthe combined organics dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customto give a light brown oil
10. customThe residue was purified on silica gel by flash column chromatography (5% MeOH in DCM, loaded in DCM, ˜200 mL silica)

ORD record

ord-a15b2c595b2c48a9ac089bc52ccc0294

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367697B2