Hydrochloric Acid → HCID 67742261, compound

HRID 1707894Notes

Reaction equation

HRID 1707894 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[C:6](I)[CH:5]=[CH:4][C:3]=1[F:10].[CH2:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]#[CH:21])=[CH:16][CH:15]=1)[CH2:12][CH3:13].Cl>C(NCC)C.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>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:21]#[C:20][C:17]2[CH:18]=[CH:19][C:14]([CH2:11][CH2:12][CH3:13])=[CH:15][CH:16]=2)=[CH:4][C:3]=1[F:10]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 27751331-Ethynyl-4-propylbenzeneHCID 189600732-Bromo-1,3-difluoro-4-iodobenzene

Product 1

HCID 67742261HCID 67742261, compoundYield 57.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Conditions

Temperature
5 °C

Procedure

2-Bromo-1,3-difluoro-4-iodobenzene (20 g) was dissolved in diethylamine (30 ml) under nitrogen atmosphere, and then bis(triphenylphosphine)palladium(II) chloride (0.06 g) and copper(I) iodide (0.06 g) were added thereto, followed by stirring. The flask was cooled to 5° C. or lower, and then 4-propylphenylacetylene (10 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 (15 ml) and ice (30 g). After extraction with chloroform, the resultant was washed with water twice, followed by distilling off chloroform. The residue was distilled under reduced pressure (b.p. 185° to 192° C./4 mmHg), and then recrystallized from a mixed solvent of acetone and methanol to give 4-bromo-3,5-difluoro-4'-propyltolane (12 g).

Workup

  1. stirringAfter stirring at room temperature for 5 hours
  2. extractionAfter extraction with chloroform
  3. washthe resultant was washed with water twice
  4. distillationby distilling off chloroform
  5. distillationThe residue was distilled under reduced pressure (b.p. 185° to 192° C./4 mmHg)
  6. customrecrystallized from a mixed solvent of acetone and methanol

Sources & evidence

ORD record
ord-2596de2562cf406ea3a98f0a2afac076
Source dataset
uspto-grants-1994_10
Patent number
US05356558

Reaction notes

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