Stannane, tributyl-3-thienyl- → HCID 19744835, compound

HRID 2254475Notes

Reaction equation

HRID 2254475 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][CH2:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11].C([Sn](CCCC)(CCCC)[C:23]1[CH:27]=[CH:26][S:25][CH:24]=1)CCC>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>[S:25]1[CH:26]=[CH:27][C:23]([C:2]2[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=2)[O:5][CH2:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH:10]=[O:11])=[CH:24]1

Participants

4

Reactant 2

HCID 10959689Stannane, tributyl-3-thienyl-HCID 19744768HCID 19744768, compound

Product 1

HCID 19744835HCID 19744835, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

1.4 g of 3-bromomethylbenzaldehyde was dissolved in 3 ml of dimethylformamide, and the solution was added to 5 ml of a tetrahydrofuran solution of phenolate, prepared from 1.5 g of 3-bromophenol and 0.36 g of 60% oily sodium hydride. The mixture was stirred for 2 hours at room temperature. The solvent was evaporated, and water and ethyl acetate were added to the residue to extract it. The extract was worked up in a customary manner to give crude 3-(3-bromophenoxymethyl)benzaldehyde. When the same reaction as in Referential Example 12 was performed using 440 mg of the resulting aldehyde compound, 747 mg of tributyl(3-thienyl)stannane and 10 mg of tetrakis(triphenylphosphine)palladium, 341 mg (yield 77%) of 3-[3-(3-thienyl)phenoxymethyl)benzaldehyde was obtained.

Workup

  1. customWhen the same reaction as in Referential Example 12

Sources & evidence

ORD record
ord-c20ae219328f451abf0958ae9422edb1
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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