1-Bromo-2-iodobenzene → HCID 19885888, compound

HRID 654941Notes

Reaction equation

HRID 654941 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[CH:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)C.[Pd](Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 114151-Bromo-2-iodobenzeneHCID 11776TriphenylphosphineHCID 1177541-Tridecyne

Product 1

HCID 19885888HCID 19885888, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 1-bromo-2-iodobenzene (5 g, 17.7 mmol), 1-tridecyne (4.9 ml, 21.2 mmol), triphenylphosphine (5 mg), palladium (II) chloride (5 mg) in triethylamine (45 ml) was refluxed under argon for 15 h. After cooling, the mixture was poured into ice-cold dilute hydrochloric acid and extracted thoroughly with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by a silica column using hexane. Fractions with Rf of about 0.36 on evaporation gave the title alkyne as a brown oil.

Workup

  1. temperaturewas refluxed under argon for 15 h
  2. temperatureAfter cooling
  3. additionthe mixture was poured into ice-cold dilute hydrochloric acid
  4. extractionextracted thoroughly with ethyl ether
  5. customEvaporation of the
  6. dry with materialdried (magnesium sulfate)
  7. customextracts gave an oil, which
  8. customwas purified by a silica column
  9. customFractions with Rf of about 0.36 on evaporation

Sources & evidence

ORD record
ord-29579ccf480441eba15f9af5ab0f8451
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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