Sodium sulfate decahydrate → 4-Bromo-2,6-diethylbenzylamine

HRID 1888422Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:15]=[C:14]([CH2:16][CH3:17])[C:11]([C:12]#[N:13])=[C:10]([CH2:18][CH3:19])[CH:9]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]([CH2:18][CH3:19])[C:11]([CH2:12][NH2:13])=[C:14]([CH2:16][CH3:17])[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under an inert atmosphere, lithium aluminum hydride (359 mg, 9.4 mmol) was suspended in anhydrous THF (9 mL) was cooled to 0° C. and then a solution of 4-bromo-2,6-diethylbenzonitrile (1.73 g, 7.36 mmol) in anhydrous THF (3 mL) was added dropwise. The reaction mixture was then allowed to warm to ambient temperature and stirring was continued for 20 h. Sodium sulfate decahydrate (6 g) was then added to quench the reaction and the resultant reaction mixture was filtered then the filtrate was then evaporated under reduced pressure. The resultant oil was purified by flash chromatography (silica, 50 g column, ISCO, 0-10% methanol in DCM) to afford the title compound as an orange oil (96 mg, 5%). 1H NMR (DMSO-D6, 400 MHz): 7.18 (s, 2H), 3.68 (s, 2H), 2.73-2.64 (m, 4H), 2.52-2.48 (m, 2H), 1.19-1.11 (m, 6H).

Workup

temperatureto warm to ambient temperature
customto quench
customthe reaction
customthe resultant reaction mixture
filtrationwas filtered
customthe filtrate was then evaporated under reduced pressure
customThe resultant oil was purified by flash chromatography (silica, 50 g column, ISCO, 0-10% methanol in DCM)

Sources & evidence

ORD record: ord-1fd2cec814ec4863b8f35679a21e5953
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501765B2

Reaction notes

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