Sodium Carbonate → Methyl 5-phenylthiophene-2-carboxylate

HRID 1835451Notes

Reaction equation

Br[C:2]1[S:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:6]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.ClCCl.[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>[CH3:10][O:9][C:7]([C:4]1[S:3][C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)=[O:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 2-bromo-5-methoxycarbonylthiophene (1.11 g) and phenylboronic acid (0.79 g) and tetrakis(triphenylphosphine)-palladium (289 mg) in 1,2-dimethoxyethane (10 ml) was added an aqueous solution of sodium carbonate (2M, 6.5 ml) followed by stirring at 80° C. for 18 hours. The mixture was diluted with dichloromethane and washed with water and brine. The mixture was dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with methanol. The resulting precipitate was collected by filtration, washed with methanol and diisopropyl ether and dried to give 2-methoxycarbonyl-5-phenylthiophene (918 mg, 84.2%).

Workup

washwashed with water and brine
dry with materialThe mixture was dried over magnesium sulfate
customevaporated under reduced pressure
customThe residue was triturated with methanol
filtrationThe resulting precipitate was collected by filtration
washwashed with methanol and diisopropyl ether
customdried

Sources & evidence

ORD record: ord-ddb17dda067a4e95ad5e1fae6d3bc5e0
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06770667B1

Reaction notes

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