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

HRID 1596693Notes

Reaction equation

HRID 1596693 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-5d37f5b56c164840b655205f54d476a9
Source dataset
uspto-grants-2001_09
Patent number
US06291621B1

Reaction notes

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