Bromopentafluorobenzene → 3-[(2,3,4,5,6-Pentafluorophenyl)ethynyl]aniline

HRID 1030868

Reaction equation

Br[C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12].[NH2:13][C:14]1[CH:15]=[C:16]([C:20]#[CH:21])[CH:17]=[CH:18][CH:19]=1>CCOCC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:12][C:3]1[C:4]([F:11])=[C:5]([F:10])[C:6]([F:9])=[C:7]([F:8])[C:2]=1[C:21]#[C:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[NH2:13]

Participants

Conditions

Temperature: 70 °C

Procedure

A multinecked flash as described in Example 1 was charged with 5.0 g (0.020 mol) of bromopentafluoro-benzene, 2.37 g (0.020 mol) of 3-aminophenylacetylene, 0.096 g (0.137 mmol) of bis(triphenylphosphine) palladium II chloride, 0.148 g (0.564 mmol) of triphenylphosphine, and 0.06 g (0.315 mmol) of cuprous iodide. The reaction mixture was heated at 70° C. for 40 hours after which gas chromatography showed the reaction to be complete. The product mixture was cooled to room temperature and diluted with 75 ml of ether. Filtration of the insoluble triethylamine hydrobromide salt by-product followed by concentration of the filtrate gave 5.7 g, (0.02 mol) of crude product as a yellow solid. Short path distillation of the crude under reduced pressure gave 2.84 g (0.010 mol, 50% yield) of the product as a colorless liquid that crystallized on standing.

Workup

customthe reaction
temperatureThe product mixture was cooled to room temperature
filtrationFiltration of the insoluble triethylamine hydrobromide salt by-product
customgave 5.7 g, (0.02 mol) of crude product as a yellow solid
distillationShort path distillation of the crude under reduced pressure

Sources & evidence

ORD record: ord-8f5f3815000a48febbaff23a56453646
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05107026

Linked notes

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