Dichloromethane → Tributyltin fluoride

HRID 2092953Notes

Reaction equation

HRID 2092953 reaction equation
S1[CH:5]=[CH:4][CH:3]=[CH:2]1.[F-:6].[Cs+].ClCCl.S1[CH:15]=[CH:14][CH:13]=[C:12]1[SnH3:16]>C1(C)C=CC=CC=1.[Pd].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>[Sn:16]([F:6])([CH2:2][CH2:3][CH2:4][CH3:5])([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 8030ThiopheneHCID 25953Cesium fluorideHCID 87207623HCID 87207623, compound

Product 1

HCID 16120Tributyltin fluoride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Introduction of the thiophene-unit to the squarylium dye framework was achieved by palladium catalyzed Stille coupling reaction. Under inert atmosphere, to a mixture of brominated squarylium dye 12, Pd(PPh3)4, 2 equivalents of CsF in toluene, thienyl-stannane was added. The reaction mixture was stirred at 120° C. for 12 h. After cooling to room temperature, dichloromethane was added. The white salt (Bu3SnF) formed during the reaction was filtered off and the solvent removed under reduced pressure. Purification of the crude product was performed by column chromatography on silica gel with (2/8) dichloromethane/ethylacetate to give the pure thiophene derived squarylium dye 13 as green solid.

Workup

  1. customreaction
  2. additionwas added
  3. temperatureAfter cooling to room temperature

Sources & evidence

ORD record
ord-183ce15494dc4cef961d52360f93d69b
Source dataset
uspto-grants-2013_05
Patent number
US08440840B2

Reaction notes

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