Water → 3-(Thiophen-3-yl)benzaldehyde

HRID 2228646Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.Br[C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14].C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.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:1]1[CH:5]=[CH:4][C:3]([C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[CH:13]=[O:14])=[CH:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

3.11 g of 3-thiopheneboronic acid (0.024 mol) are added to a solution of 3-bromobenzaldehyde (3 g, 0.016 mol) in 1,2-dimethoxyethane (80 ml), followed by addition of aqueous 2N sodium carbonate solution (5.15 g, 0.048 mol) and a catalytic amount of tetrakis(triphenylphosphine)palladium (0.56 g, 4.9 10−4 mol). The reaction mixture is heated at 80° C. for 16 hours and is then cooled to room temperature and poured into water. The resulting mixture is extracted with ethyl acetate and the organic phase is washed with saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulfate and filtered, and the solvent is evaporated off under reduced pressure. The title product is isolated by chromatography on a column of silica (eluent: 90/10 cyclohexane/ethyl acetate). 2.61 g of a pale yellow solid are recovered.

Workup

temperatureis then cooled to room temperature
extractionThe resulting mixture is extracted with ethyl acetate
washthe organic phase is washed with saturated aqueous sodium chloride solution
dry with materialThe organic phase is dried over magnesium sulfate
filtrationfiltered
customthe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record: ord-10b4d6e12b894b6c84fb6830cf10a512
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06417222B1

Reaction notes

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