Boron trifluoride etherate → DipyrroMetheneboron Difluoride

HRID 2410398Notes

Reaction equation

HRID 2410398 reaction equation
Cl.C[C:3]1[C:4](=[CH:9][C:10]2[NH:11][C:12](C)=[CH:13][C:14]=2C)[N:5]=[C:6](C)[CH:7]=1.C(N(CC)CC)C.[B:24](F)([F:26])[F:25].CCOCC>ClCCl>[B-:24]1([F:26])([F:25])[N+:5]2=[CH:6][CH:7]=[CH:3][C:4]2=[CH:9][C:10]2[N:11]1[CH:12]=[CH:13][CH:14]=2

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8471TriethylamineHCID 534118492-[(3,5-Dimethyl-2H-pyrrol-2-ylidene)methyl]-3,5-dimethyl-1H-pyrrole--hydrogen chloride (1/1)

Product 1

HCID 25058173DipyrroMetheneboron DifluorideYield 106.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(3,5-Dimethyl-2H-pyrrol-2-ylidene)methyl]-3,5-dimethyl-1H-pyrrole monohydrochloride (4 g, 16.89 mmol) was dissolved into 125 ml of dry dichloromethane to which triethylamine (17.09 g, 168.9 mmol) was added and allowed to stir for 15 minutes. The solution was then cooled with an ice bath to control the temperature during the slow addition of boron trifluoride etherate (2185 g, 168.9 mmol). Once the addition was complete, the ice bath was removed and the reaction was allowed to stir at room temperature for 2 hours. The reaction was then quenched with water and extracted three times with dichloromethane. The organic layer was then washed with saturated sodium carbonate. The organic layer was impregnated onto silica gel and then purified via column chromatography (10% dichloromethane in hexanes) to yield 3.44 g of Bodipy (82% yield).

Workup

  1. additionwas added
  2. temperatureThe solution was then cooled with an ice bath
  3. additionOnce the addition
  4. customthe ice bath was removed
  5. stirringto stir at room temperature for 2 hours
  6. customThe reaction was then quenched with water
  7. extractionextracted three times with dichloromethane
  8. washThe organic layer was then washed with saturated sodium carbonate
  9. custompurified via column chromatography (10% dichloromethane in hexanes)

Sources & evidence

ORD record
ord-19109caef6cf4e91b9ffad9d625114ce
Source dataset
uspto-grants-2014_08
Patent number
US08816095B2

Reaction notes

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