Dimethylformamide → HCID 118113146, compound

HRID 1485063Notes

Reaction equation

HRID 1485063 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.CN(C)C=O.[CH:15]1([C:18]#[CH:19])[CH2:17][CH2:16]1.[Cl-].[NH4+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(N(CC)CC)C>[CH:15]1([C:18]#[C:19][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:17][CH2:16]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 707414-BromobenzaldehydeHCID 138823Cyclopropylacetylene

Product 1

HCID 118113146HCID 118113146, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 4-bromobenzaldehyde (2.00 g), bis(triphenylphosphine)palladium(II) dichloride (228 mg), copper(I) iodide (20.6 mg), N,N-dimethylformamide (2.00 mL) and triethylamine (15.1 mL), cyclopropylacetylene was added and thereafter the mixture was stirred in a sealed tube at 110° C. for one minute under irradiation with microwaves. After being cooled to room temperature, the reaction mixture was poured into a saturated aqueous solution of ammonium chloride and extracted with a liquid mixture of n-hexane/ethyl acetate (1:1) three times. The combined organic layers were washed with saturated brine and dried over added anhydrous magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-60:40) to give 4-(cyclopropylethynyl)benzaldehyde as a brown oil (1.79 g).

Workup

  1. additionwas added
  2. temperatureAfter being cooled to room temperature
  3. extractionextracted with a liquid mixture of n-hexane/ethyl acetate (1:1) three times
  4. washThe combined organic layers were washed with saturated brine
  5. customdried
  6. additionover added anhydrous magnesium sulfate
  7. customThe desiccant was removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-60:40)

Sources & evidence

ORD record
ord-a6ac3e1b69404d8aa8fc963efe9a856d
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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