2,2'-Bipyridine → HCID 90414371, compound

HRID 1746042Notes

Reaction equation

HRID 1746042 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[O:9][C:10]([F:16])([F:15])[C:11](Br)([F:13])[F:12].N1C=CC=CC=1C1C=CC=CN=1>CS(C)=O.C(OCC)C.CCCCC.[Cu]>[F:15][C:10]1([F:16])[C:11]([F:13])([F:12])[C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=2[O:9]1

Participants

6

Reactant 2

HCID 14742,2'-BipyridineHCID 90414055HCID 90414055, compound

Product 1

HCID 90414371HCID 90414371, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolvent2×HCID 21877078Diethylether pentaneSolvent

Conditions

Temperature
150 °C

Procedure

1-Bromo-2-(2-bromo-1,1,2,2-tetrafluoroethoxy)-3-fluorobenzene (14 g, 38 mmol), copper powder (12.2 g, 192 mmol) and 2,2′-bipyridine (610 mg, 3.9 mmol) were combined in dry DMSO (55 mL) and heated to 150° C. for 1.5 h. Vacuum (ca 20 mm) was applied to the reactor and distillate was taken overhead until the pot temperature reached 100° C. The distillate containing the product and DMSO was diluted with 1:1 diethyl ether-pentane (30 mL) and washed (3×5 mL) with water, dried, and distilled at 1 atmosphere (atm) through a 200 mm Vigreux column to remove the bulk of the solvents. Vacuum (ca 20 mmHg) was applied and the fraction boiling at 60-65° C. was collected to afford the title compound as a clear liquid (5.1 g, 64%): 1H NMR (400 MHz, CDCl3) δ 7.40-7.31 (m, 2H), 7.25-7.17 (m, 1H); EIMS m/z 210.

Workup

  1. customreached 100° C
  2. washwashed (3×5 mL) with water
  3. customdried
  4. distillationdistilled at 1 atmosphere (atm) through a 200 mm Vigreux column
  5. customto remove the bulk of the solvents
  6. customthe fraction boiling at 60-65° C. was collected

Sources & evidence

ORD record
ord-1eb6190465204d53bde867435352e20d
Source dataset
uspto-grants-2015_10
Patent number
US09149038B2

Reaction notes

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