Dibromodifluoromethane → HCID 57753432, compound

HRID 225614Notes

Reaction equation

HRID 225614 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21](Br)([F:23])[F:22].[C:25]([O:29][C:30]([N:32]1[CH2:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([CH:41]=O)[CH:38]=2)[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C.[Zn]>[C:25]([O:29][C:30]([N:32]1[CH2:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([CH:41]=[C:21]([F:23])[F:22])[CH:38]=2)[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 6382DibromodifluoromethaneHCID 11776TriphenylphosphineHCID 21250554tert-Butyl 5-formyl-1,3-dihydro-2H-isoindole-2-carboxylate

Product 1

HCID 57753432HCID 57753432, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 4.69 mmol triphenylphosphine in 5 ml DMF at 0° C. was added dropwise a solution of 4.69 mmol dibromodifluoromethane in 1 ml DMF and the mixture was stirred at RT for 30 min. 2.35 mmol 5-formyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester was then added at 0° C. and then 4.69 mmol zinc dust was added in small portions. The mixture was stirred at RT for 16 and then concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a white solid (31% yield). MS (m/e): 226.1 ([M+H−Me2C═CH2]+, 100%).

Workup

  1. stirringThe mixture was stirred at RT for 16
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-0b06940317c54555b0566a567e4cb623
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

Loading…