Hydrochloric Acid → 2-Fluoro-4-[2-(4-propylphenyl)ethynyl]bromobenzene

HRID 1707892Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[F:9].[CH2:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[CH:20])=[CH:15][CH:14]=1)[CH2:11][CH3:12].Cl>C(NCC)C.[Pd](Cl)Cl.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.[Cu]I>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:20]#[C:19][C:16]2[CH:17]=[CH:18][C:13]([CH2:10][CH2:11][CH3:12])=[CH:14][CH:15]=2)=[CH:4][C:3]=1[F:9]

Participants

Conditions

Temperature: 5 °C

Procedure

1-Bromo-2-fluoro-4-iodobenzene (15 g) was dissolved in diethylamine (17 ml) under nitrogen atmosphere, and then bis(triphenylphosphine) palladium(II) chloride (0.12 g) and copper(I) iodide (0.12 g) were added thereto, followed by stirring. The flask was cooled to 5° C. or lower, and then 4-propylphenylacetylene (8 g) was added dropwise thereto. After stirring at room temperature for 5 hours, the reaction solution was poured into a mixture of concentrated hydrochloric acid (10 ml) and ice (50 g). After extraction with chloroform, the resultant was washed with water twice, followed by distilling off chloroform. The residue was recrystallized from a mixed solvent of acetone and methanol to give 4-bromo-3-fluoro-4'-propyltolane (11 g).

Workup

stirringAfter stirring at room temperature for 5 hours
extractionAfter extraction with chloroform
washthe resultant was washed with water twice
distillationby distilling off chloroform
customThe residue was recrystallized from a mixed solvent of acetone and methanol

Sources & evidence

ORD record: ord-781a226be4b644f1a899c8ab3adbf9c8
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05356558

Reaction notes

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