Borane;tetrahydrofuran → HCID 62740634, compound

To an ice-cold mixture of crude 3-(3-bromophenyl)-2,2-dimethylpropanenitrile (71) (3.0 g,12.6 mmol) in anhydrous THF (20 mL) was added BH3-THF (20 mL of a 1M solution in THF, 20 mmol) slowly. The reaction was allowed to warm slowly and stirred for 19 h. The reaction was quenched with the dropwise addition of 6 M HCl then stirred for 1.5 h. Volatiles were removed under reduced pressure. The aqueous layer was extracted with diethyl ether twice then EtOAc was added and the mixture was made basic with 5 M aqueous KOH. The layers were separated and the aqueous layer was extracted with EtOAc twice. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)-2,2-dimethylpropan-1-amine as a light yellow oil (2.3 g). This material was taken on to the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 7.32-7.35 (m, 1H), 7.30 (t, J=1.7 Hz, 1H), 7.13 (t, J=7.7 Hz, 1H), 7.06 (dd, J=7.6, 1.2 Hz, 1H), 2.50 (s, 2H), 2.47 (s, 2H), 0.84 (s, 6H).

1. temperatureto warm slowly
2. customThe reaction was quenched with the dropwise addition of 6 M HCl
3. stirringthen stirred for 1.5 h
4. customVolatiles were removed under reduced pressure
5. extractionThe aqueous layer was extracted with diethyl ether twice
6. additionEtOAc was added
7. customThe layers were separated
8. extractionthe aqueous layer was extracted with EtOAc twice
9. washThe combined organics were washed with brine
10. dry with materialdried over Na2SO4
11. concentrationconcentrated under reduced pressure

ORD record

ord-285c976fcbbb47a9b78d4d2c02085e2f

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716529B2