Dichloromethane → Tributyltin fluoride

HRID 2092952Notes

Reaction equation

C(CC(O)=O)#N.[F-:7].[Cs+].[CH2:9]([Sn:13](C1SC=CC=1)([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH3:12].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:13]([F:7])([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Conditions

Temperature: 120 °C

Procedure

1 is halogenated chromophore 2 is metalated conjugated system step a) Reaction of 1 and 2 by palladium mediated Stille coupling results in formation of compound 3; step b) The carboxylaldehyde moiety is introduced to compound 3 by Vilsmaier-Haak reaction; And step c) transformed by reaction of 4 with cyano-acetic acid to the targeted 5. 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 (2/8) dichloromethane/ethylacetate to give the pure thiophene derived squarylium dye 3. Analytical Data for 3

Workup

additionwere added
temperatureAfter cooling to room temperature

Sources & evidence

ORD record: ord-556cb059fcf94d40b352be07c7fff280
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440840B2

Reaction notes

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