Cesium carbonate → HCID 86714199, compound

HRID 628210Notes

Reaction equation

HRID 628210 reaction equation
I[C:2]1[S:6][C:5]2[CH:7]=[C:8]3[C:13](=[CH:14][C:4]=2[CH:3]=1)[CH:12]=[CH:11][CH:10]=[CH:9]3.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.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>[C:4]1([CH:3]=[CH:2][C:2]2[S:6][C:5]3[CH:7]=[C:8]4[C:13](=[CH:14][C:4]=3[CH:3]=2)[CH:12]=[CH:11][CH:10]=[CH:9]4)[CH:14]=[CH:13][CH:8]=[CH:7][CH:5]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 86714200HCID 86714200, compound

Product 1

HCID 86714199HCID 86714199, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 4,4,5,5-Tetramethyl-2-[(1E)-2-(phenylethenyl]-1,3,2-dioxaborolane (15, 1.62 g, 7.04 mmol), 2-iodonaphtho[2,3-b]thiophene (5, 1.04 g, 3.35 mmol), Cs2CO3 (6.53 g, 20.04 mmol), and Pd(PPh3)4 (154.5 mg, 0.134 mmol, 4% mol) in dry DMF (70 mL) was heated at 80° C. for overnight for 2 days. The reaction mixture was then allowed to cool to room temperature, the formed precipitate was filtered and washed with methanol, water, and hexanes to yield a green crude solid. The crude solid was purified by vacuum sublimation in high vacuum (Tsub=250° C.) to give PVNT as an off-white solid (480 mg, 50% yield). 1H NMR (500 MHz, C2D2Cl4) δ 8.24 (s, 1H), 8.15 (s, 1H), 7.96 (m, 1H), 7.89 (m, 1H), 7.45 (m, 5H), 7.34 (s, 1H), 7.32 (d, J=16.0 Hz, 1H), 7.21 (d, J=8.0 Hz, 2H), 6.98 (d, J=16 Hz, 1H). Anal. calcd. for (C20H14S): C, 83.88; H, 4.93. Found: C, 84.37; H, 4.74. m.p. 305-307° C.

Workup

  1. filtrationthe formed precipitate was filtered
  2. washwashed with methanol, water, and hexanes
  3. customto yield a green crude solid
  4. customThe crude solid was purified by vacuum sublimation in high vacuum (Tsub=250° C.)

Sources & evidence

ORD record
ord-6456f17f578148aebe4881f9d33dbcf5
Source dataset
uspto-grants-2016_04
Patent number
US09312501B2

Reaction notes

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