5-Bromo-2-iodotoluene → HCID 57201412, compound

HRID 1821042Notes

Reaction equation

HRID 1821042 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH3:8])[CH:7]=1.C([Sn](CCCC)(CCCC)[C:15]1[S:16][CH:17]=[CH:18][N:19]=1)CCC>C1COCC1.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>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 2

HCID 27246015-Bromo-2-iodotolueneHCID 27632592-(Tributylstannyl)-1,3-thiazole

Product 1

HCID 57201412HCID 57201412, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 5-bromo-2-iodotoluene (0.15 g, 1.18 mmol) and 2-tributylstannylthiazole (0.45 g, 1.18 mmol) in THF (4 mL) in a sealed tube was degassed with a balloon of argon for 5 min. Bis(triphenylphosphine)palladium(II) chloride (1.18 mmol) was added, the reaction was capped and heated at 90° C. for 6 h. Silica gel chromatography eluting with 100% hexanes yielded 0.12 g of desired product: 1H NMR (500 MHZ, CDCl3) δ 7.95 (d, J=3.0 Hz, 1H), 7.63 (d, J=8.3 Hz, 1H), 7.50 (s, 1H), 7.44 (d, J=2.8 Hz, 2H), 2.60 (s, 3H).

Workup

  1. customthe reaction was capped
  2. washSilica gel chromatography eluting with 100% hexanes

Sources & evidence

ORD record
ord-f31b0bdcfca74693840c926f8000450f
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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