Dichloromethane → Tributyltin fluoride

HRID 2095091Notes

Reaction equation

HRID 2095091 reaction equation
[F-:1].[Cs+].[CH2:3]([Sn:7](C1SC=CC=1)([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH2:10][CH3:11])[CH2:4][CH2:5][CH3:6].ClCCl>C1(C)C=CC=CC=1.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:7]([F:1])([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 25953Cesium fluorideHCID 27793732-(Tri-n-butylstannyl)thiophene

Product 1

HCID 16120Tributyltin fluoride

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Step a) Under inert atmosphere, to a mixture of chromophore 1, 1 mol % catalysator Pd(PPh3)4, 1 equivalent of CsF in toluene, 1.2 equivalent of tributylstannyl-thiophene were 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 (4/6) dichloromethane/ethylacetate to give the pure thiophene derived squarylium dye 3.

Workup

  1. additionwere added
  2. temperatureAfter cooling to room temperature

Sources & evidence

ORD record
ord-ea42147f6c074fd695aa45671a045f76
Source dataset
uspto-grants-2013_05
Patent number
US08445697B2

Reaction notes

Loading…