2-(Tri-n-butylstannyl)thiophene → HCID 22996753, compound

HRID 278503Notes

Reaction equation

HRID 278503 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([O:14][CH3:15])[CH:9]=[CH:10][C:11]=2Br)[C:6](Br)=[CH:5][CH:4]=1.C([Sn](CCCC)(CCCC)[C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([O:14][CH3:15])[CH:9]=[CH:10][C:11]=2[C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)[C:6]([C:24]2[S:23][CH:22]=[CH:26][CH:25]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 11131763Naphthalene, 1,5-dibromo-4,8-dimethoxy-

Product 1

HCID 22996753HCID 22996753, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

1,5-Dimethoxy-4,8-dibromonaphthalene (1.19 g., 0.0034 mol.) and 2-(tributylstannyl)thiophene (3.85 g., 0.0103 mol.) were dissolved in 100 mL dry toluene in argon atmosphere. Pd(PPh3)4 (100 mg.) was introduced into the reaction flask using a Schlenk tube under argon. The resultant mixture was subsequently refluxed for 18 hrs. The brownish black solution was cooled and poured into 300 mL of petroleum ether to afford crude yellow solid. Upon recrystallization from CH2Cl2:petroleum ether (1:5), the desired product was obtained as a light yellow solid. Yield: 81%. M. p. 216-218° C. Anal. Calcd. for C20H16O2S2: C, 68.15%; H, 4.58%; S, 18.19%. Found: C, 67.64%; H, 4.48%; S, 17.49%. Mass spectrum: 351.75 (M+). 1H-NMR (CDCl3; in ppm): 3.59 (s, 3H), 6.81 (d, 2H), 6.89 (d, 2H), 7.00 (dd, 2H), 7.26 (dd, 2H), 7.38 (d, 2H). 13C-NMR (CDCl3; in ppm): 55.6, 106.5, 123.1, 123.5, 125, 125.5, 126.1, 131.1, 147.5, 156.8.

Workup

  1. temperatureThe brownish black solution was cooled
  2. customto afford crude yellow solid
  3. customUpon recrystallization from CH2Cl2:petroleum ether (1:5)

Sources & evidence

ORD record
ord-b4fdad51e96b4fcd895ca959e33dbb9e
Source dataset
uspto-grants-2002_03
Patent number
US06359149B1

Reaction notes

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