Hydrochloric Acid → 4-(4-(Isopropylthio)phenyl)thiophene-2-carboxylic acid

HRID 1892088Notes

Reaction equation

[CH:1]([S:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Br[C:15]1[CH:16]=[C:17]([C:20]([OH:22])=[O:21])[S:18][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(#N)C>[CH:1]([S:4][C:5]1[CH:10]=[CH:9][C:8]([C:15]2[CH:16]=[C:17]([C:20]([OH:22])=[O:21])[S:18][CH:19]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of commercially available 4-(isopropylthio)phenylboronic acid (735 mg, 3.75 mmol), 4-bromothiophene-2-carboxylic acid (776 mg, 3.75 mmol), Bis(triphenylphosphine)palladium (II) chloride (131 mg, 0.188 mmol), acetonitrile (7.5 mL) and aqueous sodium carbonate (1M, 7.5 mL) was heated to 150° C. by microwave irradiation (Biotage Intiator™ Sixty, 0-300 W, pre-stirring 2 minutes) for 5 minutes under an argon atmosphere. The reaction mixture was cooled to ambient temperature, diluted with water (75 mL), and extracted with EtOAc (2×50 mL). The aqueous layer obtained was then acidified with aqueous HCl (3.0M) to pH 2 and extracted with EtOAc (2×50 mL). The combined organic layers were dried over sodium sulfate, filtrated and concentrated to afford compound 73 (990 mg) which was used in next step without further purification.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
extractionextracted with EtOAc (2×50 mL)
customThe aqueous layer obtained
extractionextracted with EtOAc (2×50 mL)
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltrated
concentrationconcentrated

Sources & evidence

ORD record: ord-942244332d5d4e449cdb5b932a70b9db
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507647B2

Reaction notes

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