2-(Tri-n-butylstannyl)thiophene → HCID 22996756, compound

HRID 1596695Notes

Reaction equation

HRID 1596695 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([O:16][CH3:17])[C:9](Br)=[CH:10][C:11]=2[O:13][CH3:14])[C:6]([O:18][CH3:19])=[CH:5][C:4]=1Br.C([Sn](CCCC)(CCCC)[C:26]1[S:27][CH:28]=[CH:29][CH:30]=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:16][CH3:17])[C:9]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[CH:10][C:11]=2[O:13][CH3:14])[C:6]([O:18][CH3:19])=[CH:5][C:4]=1[C:28]1[S:27][CH:26]=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 143603142,6-Dibromo-1,4,5,8-tetramethoxynaphthalene

Product 1

HCID 22996756HCID 22996756, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

1,4,5,8-Tetramethoxy-2,6-dibromonaphthalene (7.80 g., 0.019 mol.) and 2-(tributylstannyl)thiophene (18.00 g., 0.048 mol.) were dissolved in 200 mL dry toluene under 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 500 mL of petroleum ether to afford crude yellow solid. Upon recrystallization from CH2Cl2/petroleum ether (1:3) the desired product was obtained as a light yellow solid. Yield: 96%. M.p. 233.5-237° C. Anal. Calcd. for C22H20O4S2: C, 64.06%; H, 4.89%; S, 15.54%. Found: C, 64.12%; H, 4.90%; S, 15.12%. Mass spectrum: 411.84 (M+). 1H-NMR (CDCl3; in ppm.): 3.73 (s, 3H), 4.05 (s, 3H), 7.13 (dd, 2H), 7.19 (s, 2H), 7.41 (dd, 2H), 759 (dd, 2H,). 13C-NMR (CDCl3; in ppm.): 56.7, 61.7, 107.5, 122.5, 124.4, 125.7, 126.6, 126.9, 139.1, 146.5, 152.5.

Workup

  1. temperatureThe brownish black solution was cooled
  2. customto afford crude yellow solid
  3. customUpon recrystallization from CH2Cl2/petroleum ether (1:3) the desired product
  4. customwas obtained as a light yellow solid

Sources & evidence

ORD record
ord-0bee9325f4ed4613bacb9788e1d486d9
Source dataset
uspto-grants-2001_09
Patent number
US06291621B1

Reaction notes

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