HCID 18956456, compound → HCID 18956464, compound

HRID 2380008Notes

Reaction equation

HRID 2380008 reaction equation
Br[C:2]([F:33])([F:32])[C:3](F)([F:30])[O:4][C:5]1[CH:29]=[CH:28][CH:27]=[C:7]2[C:8]([N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20](F)([F:25])[C:21]([F:24])([F:23])Br)=[CH:15][CH:14]=3)[C:11](=[O:12])[C:6]=12)=[O:9]>C(#N)C.[Zn]>[F:30][C:3]([O:4][C:5]1[CH:29]=[CH:28][CH:27]=[C:7]2[C:8]([N:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][C:20]([F:25])=[C:21]([F:23])[F:24])=[CH:17][CH:18]=3)[C:11](=[O:12])[C:6]=12)=[O:9])=[C:2]([F:33])[F:32]

Participants

4

Reactant 1

HCID 18956456HCID 18956456, compound

Product 1

HCID 18956464HCID 18956464, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6342AcetonitrileSolvent2×

Procedure

The product of the previous preparation, 3-(2-Bromotetrafluoroethoxy)-N-(4-(2-bromotetrafluoroethoxy)phenyl) phthalimide, (2.73 g, 0.00445 mole) is dissolved in 20 ml of warm acetonitrile (approximately 50° C.) and added to zinc metal (0.61 g, 0.0093 mole) in 5 ml of acetonitrile stirring at reflux. The reaction mixture is stirred at reflux for 12 hours, then filtered on a fine-pored fritted glass funnel to remove unreacted zinc and zinc halide salts. The precipitate is washed twice with 25 ml of dichloromethane, and the filtrates are combined with the acetonitrile flitrate and evaporated to dryness. The dry residue is dissolved in 15 ml of dichloromethane/hexane (1:1, v/v (volume/volume)) and subjected to column chromatography on neutral alumina using dichloromethane/hexane (1:4, v/v) to provide the product (1.54 g, 83.4 percent yield) as a light yellow solid with a melting point of 160°-160.5° C. IR (cm-1): 1721, 1708, 1322, 1121 (imide), 1289, 1282, 1273, 1213, 1191, 1166, 1146, 1110, 1096 (C-O, C-F), 1514, 808, 801,743 (aromatic).

Workup

  1. temperatureat reflux
  2. temperatureat reflux for 12 hours
  3. filtrationfiltered on a fine-pored fritted glass funnel
  4. customto remove unreacted zinc and zinc halide salts
  5. washThe precipitate is washed twice with 25 ml of dichloromethane
  6. customevaporated to dryness
  7. dissolutionThe dry residue is dissolved in 15 ml of dichloromethane/hexane (1:1, v/v (volume/volume))

Sources & evidence

ORD record
ord-dd0d718c15434e9dbecf6873d223fc05
Source dataset
uspto-grants-1994_11
Patent number
US05364917

Reaction notes

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