Potassium Carbonate → (5-Bromo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile

HRID 81741

Reaction equation

[Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([CH:9]([CH3:11])[CH3:10])=[C:6]([OH:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:21][C:22]#[N:23]>CN(C)C=O.O>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([CH:9]([CH3:11])[CH3:10])=[C:6]([CH:7]=1)[O:8][CH2:21][C:22]#[N:23]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 5-bromo-2-isopropyl-4-methoxy-phenol from step 4 (0.831 g, 3.4 mmol) and K2CO3 (0.562 g, 4.1 mmol) in 17 mL dimethyl formamide (DMF) was added iodoacetonitrile (0.594 g, 3.6 mmol). The mixture was warmed to 60° C. for 30 minutes and then allowed to cool to room temperature. After cooling to room temperature the mixture was taken up in 50 mL of H2O and extracted with 1:1 toluene/ethyl acetate, washed with H2O and then with brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give a crude solid. Purification via flash chromatography (1:1 hexane/CH2Cl2) afforded (5-bromo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile (0.611 g, 63%) as a while solid.

Workup

temperatureto cool to room temperature
temperatureAfter cooling to room temperature the mixture
extractionextracted with 1:1 toluene/ethyl acetate
washwashed with H2O
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a crude solid
customPurification via flash chromatography (1:1 hexane/CH2Cl2)

Sources & evidence

ORD record: ord-f36638fc0db549a89ebf1cd613d71525
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846705B2

Linked notes

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