2-Iodothiophene → 5-Phenoxy-2-thiophenecarboxylic acid

HRID 894235Notes

Reaction equation

IC1SC=CC=1.C[O-].[O-]CC.[O-:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O[C:20]1[S:24][C:23]([C:25]([OH:27])=[O:26])=[CH:22][CH:21]=1>>[O:12]([C:20]1[S:24][C:23]([C:25]([OH:27])=[O:26])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Reactant 5

HCID 189212-Iodothiophene

HCID 119047Phenolate

HCID 1194401-Hydroxyethyl radical

HCID 3826051Methoxide

HCID 21162480HCID 21162480, compound

Product 1

HCID 223505065-Phenoxy-2-thiophenecarboxylic acid

Procedure

The latter compounds are alternatively prepared by reaction of 2-iodothiophene with methoxide, ethoxide or phenoxide, followed by carbonylation according to Sice [J. Am. Chem. Soc. 75, 3697 (1953)], or by alkylation of 5-hydroxythiophene-2-carboxylic acid by the method of Gronowitz [Ankiv Kemi 12, 239 (1958); Chem. Abstr. 52, 20115].

Sources & evidence

ORD record: ord-e65309565c214cd386596b29dd2030d8
Source dataset: uspto-grants-1981_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04282246

Reaction notes

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