Hydrochloric Acid → 5-Bromo-2-(3-furanyl)-3-thiophenecarboxylic acid

HRID 1967100Notes

Reaction equation

Br[C:2]1[S:3][C:4]([Br:10])=[CH:5][C:6]=1[C:7]([OH:9])=[O:8].C([O-])([O-])=O.[K+].[K+].[O:17]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18]1.Cl>O1CCOCC1.O.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>[Br:10][C:4]1[S:3][C:2]([C:19]2[CH:20]=[CH:21][O:17][CH:18]=2)=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2,5-dibromo-3-thiophenecarboxylic acid (750 mg, 1.38 mmol)[prepared according to Goto, Hiromasa; Dai, Xiaoman; Narihiro, Harunori; Akagi, Kazuo Macromolecules 2004 37, 7, 2353-2362.] in dioxane/H2O (5:1, 6 mL) was added K2CO3 (486 mg, 3.52 mmol), tetrakistriphenylphosphine Pd(0) (51 mg, 44 umol), and 3-furanboronic acid (108 mg, 0.968 mmol). The reaction mixture was heated to 80° C. in a sealed tube. After 12 h, the solution was poured onto H2O (100 mL) and the pH was adjusted to ˜4 with aqueous HCl. The aqueous phase was extracted several times with DCM and the combined organic fractions were dried (Na2SO4), concentrated under vacuum and used directly: LC-MS (ES) m/z=273.

Workup

additionthe solution was poured onto H2O (100 mL)
extractionThe aqueous phase was extracted several times with DCM
dry with materialthe combined organic fractions were dried (Na2SO4)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-7fc9c82ce8e445a1bb69c28600250fbc
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420690B2

Reaction notes

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