Potassium Fluoride → 4-Bromo-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrile

HRID 1472771Notes

Reaction equation

HRID 1472771 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[N:9])[S:5][C:6]=1Br.[CH3:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](B(O)O)=[CH:13][CH:12]=1.[F-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[N:9])[S:5][C:6]=1[C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]([CH3:10])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 27735114-Methyl-1-naphthaleneboronic acidHCID 232622764,5-Dibromothiophene-2-carbonitrile

Product 1

HCID 682936224-Bromo-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrileYield 88.4%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

A round-bottomed flask was charged with 4,5-dibromothiophene-2-carbonitrile (536 mg, 2.00 mmol), 4-methylnaphthalen-1-ylboronic acid (409 mg, 2.20 mmol), Pd2(dba)3 (18.3 mg, 0.020 mmol) and KF (383 mg, 6.60). After degassed, dioxane (5 mL) and P(Bu-t)3 (0.24 mL, 0.2M, 0.048 mmol) was added. The reaction mixture was stirred at rt until complete. 30 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=3:1). 0.58 g (88%) of product was obtained as a white solid.

Workup

  1. customAfter degassed
  2. additiondioxane (5 mL) and P(Bu-t)3 (0.24 mL, 0.2M, 0.048 mmol) was added
  3. addition30 mL of water was added
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (hexane:CH2Cl2=3:1)

Sources & evidence

ORD record
ord-99eaff835a184249a65a657b5e3a0282
Source dataset
uspto-grants-2015_04
Patent number
US09012655B2

Reaction notes

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