1,4-Dibromo-2,5-diiodobenzene → HCID 58340348, compound

HRID 2369719Notes

Reaction equation

HRID 2369719 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](I)[C:5]([Br:9])=[CH:4][C:3]=1I.[Br-:11].[Br:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[Zn+]>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.O1CCCC1>[Br:1][C:2]1[CH:7]=[C:6]([C:14]2[S:15][CH:16]=[CH:17][C:13]=2[Br:12])[C:5]([Br:9])=[CH:4][C:3]=1[C:14]1[S:15][CH:16]=[CH:17][C:13]=1[Br:11]

Participants

5

Reactant 2

HCID 111237711,4-Dibromo-2,5-diiodobenzeneHCID 178419764HCID 178419764, compound

Product 1

HCID 58340348HCID 58340348, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
85 °C

Procedure

A oven dried 2000 cm3 flask is charged with 1,4-dibromo-2,5-diiodobenzene (61.00 g, 125.1 mmol), dichlorobis(triphenylphosphine)palladium(II) (2.195 g, 3.127 mmol) and anhydrous tetrahydrofuran (300 cm3). Once the starting materials are dissolved, a solution of 0.5 M of 3-bromo-2-thienylzinc bromide in tetrahydrofuran (500 cm3, 250.2 mmol) is transfered using a canula and the reaction heated to 85° C. for 3 hours. The reaction is cooled down overnight and the white precipitate filtered off. This precipitate is washed with water (750 cm3) and methanol (250 cm3) to obtain 25.77 g of the title product. Further product is recovered from the initial filtrate. The filtrate is reduced to ca. 90 cm3 in vacuo and then 500 cm3 of methanol is added. The precipitate is filtered off, washed with water (750 cm3) and methanol (250 cm3) and finally triturated three times in hot propan-2-ol to obtain an additional 12.72 g of the title product. (38.49 g, Yield: 55%). NMR (1H, 300 MHz, CDCl3): δ 7.71 (s, 2H); 7.42 (d, J=5.3 Hz, 2H); 7.09 (d, J=5.3 Hz, 2H). NMR (13C, 75 MHz, CDCl3): δ 136.62; 136.10; 135.16; 130.50; 126.97; 123.52; 111.78.

Workup

  1. customA oven dried 2000 cm3 flask
  2. dissolutionOnce the starting materials are dissolved
  3. temperatureThe reaction is cooled down overnight
  4. filtrationthe white precipitate filtered off
  5. washThis precipitate is washed with water (750 cm3) and methanol (250 cm3)

Sources & evidence

ORD record
ord-d60e03e3834448438c42dcd62917b817
Source dataset
uspto-grants-2014_04
Patent number
US08709290B2

Reaction notes

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