tert-Butanol → HCID 10824050, compound

HRID 592427Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH3:12])([CH3:11])[C:9]#[N:10].[OH-].[Na+].CC([OH:19])(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH3:12])([CH3:11])[C:9]([NH2:10])=[O:19]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(2-bromophenyl)-2-methylpropanenitrile A33 (0.377 g, 1.68 mmol), NaOH (0.135 g, 3.37 mmol) and t-BuOH (4 mL) was stirred in a sealed vessel at 100° C. for 40 hours. The reaction mixture was cooled, diluted with DCM and filtered through Celite. The filtrate solvent was removed in vacuo and the residue was purified by column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A34 as a colourless oil (0.192 g, 48%). LCMS-D: rt 3.06 min; m/z 242/244 [M+H]+.

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered through Celite
customThe filtrate solvent was removed in vacuo
customthe residue was purified by column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record: ord-d46c155a55d94e368534fccfcf0e36cd
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238644B2

Reaction notes

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