Stannane, tributyl-3-thienyl- → 5-(3-Thienyl)-3-thiophenecarboxylic acid ethyl ester

HRID 2254480Notes

Reaction equation

HRID 2254480 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9](Br)[S:8][CH:7]=1)=[O:5])[CH3:2].C([Sn](CCCC)(CCCC)[C:17]1[CH:21]=[CH:20][S:19][CH:18]=1)CCC>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)[S:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 10959689Stannane, tributyl-3-thienyl-HCID 15293216Ethyl 5-bromothiophene-3-carboxylate

Product 1

HCID 545742635-(3-Thienyl)-3-thiophenecarboxylic acid ethyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

The same reaction as in Referential Example 37 was carried out except using 380 mg of 5-bromo-3-thiophenecarboxylic acid ethyl ester [see J. Am. Chem. Soc., 26, 2446 (1954)], 730 mg of tributyl(3-thienyl)stannane and 10 mg of tetrakis(triphenylphosphine) palladium to give 172 mg (yield 51%) of 5-(3-thienyl)-3-thiophenecarboxylic acid ethyl ester.

Workup

  1. customThe same reaction as in Referential Example 37

Sources & evidence

ORD record
ord-2cf52f0aaa3747f5921658e97a0e6181
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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