HCID 131719027, compound → 4,4'-Bis(trifluoroethenyloxy)-alpha-methylstilbene

HRID 21997Notes

Reaction equation

HRID 21997 reaction equation
BrC(F)(F)C(F)(F)O[C:5]1([O:20][C:21](F)([F:26])[C:22]([F:25])([F:24])Br)[CH:10]=[CH:9][C:8]([C:11]([CH3:19])=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH2:6]1>[Zn].C(#N)C>[F:26][C:21]([O:20][C:5]1[CH:6]=[CH:7][C:8]([C:11]([CH3:19])=[CH:12][C:13]2[CH:14]=[CH:15][C:16]([O:20][C:21]([F:26])=[C:22]([F:25])[F:24])=[CH:17][CH:18]=2)=[CH:9][CH:10]=1)=[C:22]([F:25])[F:24]

Participants

4

Reactant 1

HCID 131719027HCID 131719027, compound

Product 1

HCID 544170224,4'-Bis(trifluoroethenyloxy)-alpha-methylstilbene

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
75 °C

Procedure

The intermediate product 4,4-bis(2-bromotetrafluoroethoxy)-α-methylstilbene (106.43 g, 0.18 mole) is added to 100 ml of acetonitrile in a 250 ml dropping addition funnel attached to a 1 liter 5-necked round bottomed flask. Zinc granules (40 mesh, 25.0 g, 0.38 mole) are added to the reactor along with 100 ml of acetonitrile, and the resulting stirred suspension is deoxygenated with nitrogen for 10 minutes by introducing nitrogen gas through a gas dispersion tube. The suspension is then heated to 75° C., at which point the addition of intermediate product solution in acetonitrile is begun. The addition is carried out over 20 minutes, and the resulting mixture is heated at 75° C. overnight. After centrifugation to remove suspended solids, the resulting supernatant is evaporated to dryness, leaving a crude product which is filtered through a short bed (4 cm) of alumina in a 600 ml sintered glass filter funnel using hexane as the eluent. After removal of the hexane by evaporation, the product is heated at 55° C. under high vacuum for 30 minutes.

Workup

  1. additionaddition funnel
  2. customattached to a 1 liter 5-necked round bottomed flask
  3. customis deoxygenated with nitrogen for 10 minutes
  4. additionby introducing nitrogen gas through a gas dispersion tube
  5. additionthe addition of intermediate product solution in acetonitrile
  6. additionThe addition
  7. temperaturethe resulting mixture is heated at 75° C. overnight
  8. customAfter centrifugation to remove
  9. customthe resulting supernatant is evaporated to dryness

Sources & evidence

ORD record
ord-e8ffe7707e514ba896b725fa533b8b66
Source dataset
uspto-grants-1995_06
Patent number
US05426164

Reaction notes

Loading…