Triethylamine → HCID 90314138, compound

HRID 1505750Notes

Reaction equation

HRID 1505750 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH:14]1([C:17]#[CH:18])[CH2:16][CH2:15]1.C(N(CC)CC)C>CN(C=O)C.C1(C)C=CC=CC=1.[Cu](I)I.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>[Cl:13][C:5]1[CH:4]=[CH:3][C:2]([C:18]#[C:17][CH:14]2[CH2:16][CH2:15]2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 138823CyclopropylacetyleneHCID 144749Ethyl 5-bromo-2-chlorobenzoate

Product 1

HCID 90314138HCID 90314138, compoundYield 103.7%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 5-bromo-2-chlorobenzoate (1.9 g) in DMF (12 mL), toluene (0.3 mL), cyclopropylacetylene (714 mg), copper iodide (275 mg), dichloro bis(triphenylphosphine)palladium (1.01 g) and triethylamine (20.1 mL) were added, and the mixture was degassed, stirred at 100° C. under argon atmosphere for 8 hours, and then the reaction mixture was cooled to room temperature and diluted with ethyl acetate. The insoluble material was filtered off on celite. The mother liquor was washed with brine, dried over magnesium sulfate and concentrated. By purification on column chromatography, ethyl 2-chloro-5-(cyclopropylethynyl)benzoate (1.86 g) was obtained as brown oil.

Workup

  1. customthe mixture was degassed
  2. temperaturethe reaction mixture was cooled to room temperature
  3. additiondiluted with ethyl acetate
  4. filtrationThe insoluble material was filtered off on celite
  5. washThe mother liquor was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customBy purification on column chromatography

Sources & evidence

ORD record
ord-560e49dc0ade4467833eb5257c93f891
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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