Hydrochloric Acid → HCID 43528776, compound

To a solution of 2-(tert-butylthio)benzonitrile (Guiu, E. et al., J. Organomet. Chem., 689:1911-1918 (2004)) (1.00 g, 5.23 mmol) in THF (10.5 mL) was added BH3.THF (10.5 mL, 10.5 mmol, 1.0M solution in THF) via syringe. The resulting clear, colorless solution was stirred at room temperature for 1.5 h and then at 50° C. for 2 h. The reaction mixture was cooled to room temperature, and MeOH (2.5 mL) was added carefully via syringe (gas evolution) followed by 1N aq. HCl solution (12.0 mL). The mixture was poured into EtOAc and the layers were separated. The aqueous layer was basified with 1N aq. NaOH solution (pH=12) and then extracted with CH2Cl2 (5×). The combined CH2Cl2 extracts were dried over MgSO4, filtered and concentrated in vacuo to give the title compound (288 mg, 28%) as a colorless oil. 1H NMR (CDCl3) δ 7.57-7.53 (m, 1H), 7.44-7.40 (m, 1H), 7.37-7.32 (m, 1H), 7.25-7.19 (m, 1H), 4.07 (s, 2H), 1.30 (s, 9H); MS(ESI+) m/z 196.2 (M+H)+.

1. waitat 50° C. for 2 h
2. temperatureThe reaction mixture was cooled to room temperature
3. customthe layers were separated
4. extractionextracted with CH2Cl2 (5×)
5. dry with materialThe combined CH2Cl2 extracts were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-73ec33d3e0d64c0cb1fe952f1347c14f

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346795B2