Sodium Carbonate → 4,5-Bis(4-chloro-2-methylphenyl)thiophene-2-carbonitrile

HRID 1472769Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]#[N:9])[S:5][C:6]=1Br.[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[C:13]([CH3:20])[CH:12]=1.O1[CH2:26][CH2:25]OCC1.C(=O)([O-])[O-].[Na+].[Na+]>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.O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:3]=[C:4]([C:8]#[N:9])[S:5][C:6]=2[C:14]2[CH:13]=[CH:12][C:11]([Cl:10])=[CH:16][C:25]=2[CH3:26])=[C:13]([CH3:20])[CH:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A round-bottomed flask was charged with 4,5-dibromothiophene-2-carbonitrile (534 mg, 2.00 mmol), 4-chloro-2-methylphenylboronic acid (818 mg, 4.80 mmol) and Pd(PPh3)4 (136 mg, 0.10 mmol). After degassed, dioxane (10 mL) and aqueous sodium carbonate (5 mL, 2M, 10 mmol) was added. The reaction mixture was heated to 90° C. The progress of the reaction was monitored by TLC. After the reaction was complete, 50 mL of water was added, and the reaction mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and then concentrated. The residue was purified by flash chromatography (hexane:CH2Cl2=2:1). 0.60 g (84%) of product was obtained as clear oil.

Workup

customAfter degassed
extractionthe reaction mixture was extracted with ethyl acetate
dry with materialThe organic phase was dried over anhydrous sodium sulphate
concentrationconcentrated
customThe residue was purified by flash chromatography (hexane:CH2Cl2=2:1)

Sources & evidence

ORD record: ord-8bdaa99b9d2843429bd42ddfd2ead309
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012655B2

Reaction notes

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