Dimethylformamide → HCID 57969743, compound

HRID 384071Notes

Reaction equation

[Li+].[Cl-].C1C[O:6][CH2:5]C1.Br[C:9]1[CH:10]=[C:11]([C:16]2([C:19]#[N:20])[CH2:18][CH2:17]2)[CH:12]=[C:13]([Br:15])[CH:14]=1.CN(C=O)C.[NH4+].[Cl-]>O.C(OCC)(=O)C>[Br:15][C:13]1[CH:12]=[C:11]([C:16]2([C:19]#[N:20])[CH2:18][CH2:17]2)[CH:10]=[C:9]([CH:5]=[O:6])[CH:14]=1

Participants

Conditions

Temperature: -20 °C

Procedure

LiCl in THF (5.429 mL of 14% w/v, 5.233 mmol) was placed in an oven-dried 3-necked flask under nitrogen. The flask was cooled to −20° C. and 1-(3,5-dibromophenyl)cyclopropane-1-carbonitrile (1.5 g, 4.984 mmol) was added in one portion. The temperature was maintained between −20 and −10° C. for 90 minutes. DMF (400.7 mg, 424.5 μL, 5.482 mmol) was then added and the reaction allowed to warm to room temperature overnight. NH4Cl (sat. aq. soln.) was added followed by ethyl acetate and water. The mixture was extracted three times with ethyl acetate, the combined organics dried over MgSO4 and the solvent removed under reduced pressure. The crude product was purified on silica (Companion, 24 g) eluting with 2-30% EtOAc:Petrol ether to give 1-(3-bromo-5-formyl-phenyl)cyclopropane-1-carbonitrile as a white solid (1.037 g, 83%).

Workup

temperatureThe temperature was maintained between −20 and −10° C. for 90 minutes
temperatureto warm to room temperature overnight
extractionThe mixture was extracted three times with ethyl acetate
dry with materialthe combined organics dried over MgSO4
customthe solvent removed under reduced pressure
customThe crude product was purified on silica (Companion, 24 g)
washeluting with 2-30% EtOAc

Sources & evidence

ORD record: ord-605467200f224a8b8141be5456879b65
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367697B2

Reaction notes

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