Triethylamine → HCID 69670919, compound

HRID 1191640Notes

Reaction equation

HRID 1191640 reaction equation
Br[C:2]1[CH:8]=[C:7]([O:9][C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][C:3]=1[NH2:4].[I-].C(N(CC)CC)C.[C:22]1([C:28]#[CH:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:22]1([C:28]#[C:29][NH:4][C:3]2[CH:5]=[CH:6][C:7]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:8][CH:2]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 30165Iodide IonHCID 6882962-Bromo-4-(trifluoromethoxy)aniline

Product 1

HCID 69670919HCID 69670919, compound

Reagents, catalysts & solvents 3

HCID 178419050HCID 178419050, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-bromo-4-trifluoromethoxyaniline (0.500 g), cupper iodide (I) (18.6 mg), bis(triphenylphosphine)palladium (II) dichloride (68.5 mg), triethylamine (0.817 mL) and tetrahydrofuran (7.8 mL) was added phenylacetylene (0.279 mL) at room temperature under stirring, and the mixture was stirred at 80° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with diethyl ether (30 mL) and then filtered through celite (registered trademark). The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (206 mg).

Workup

  1. stirringthe mixture was stirred at 80° C. for 16 hours
  2. filtrationfiltered through celite (registered trademark)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-d9926286bda947c58406469e41ab52f6
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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