4-Fluorostyrene → 2-(2,6-Difluorophenyl)-4-[4-[2-(4-fluorophenyl)ethenyl]phenyl]-4,5-dihydrooxazole

HRID 964317Notes

Reaction equation

HRID 964317 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=2)[N:13]=1.[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[CH2:27])=[CH:24][CH:23]=1.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([CH:27]=[CH:26][C:25]3[CH:28]=[CH:29][C:22]([F:21])=[CH:23][CH:24]=3)=[CH:16][CH:15]=2)[N:13]=1

Participants

6

Reactant 3

HCID 678834-FluorostyreneHCID 80271Tri-o-tolylphosphineHCID 11058111Oxazole, 2-(2,6-difluorophenyl)-4,5-dihydro-4-(4-iodophenyl)-

Product 1

HCID 702005862-(2,6-Difluorophenyl)-4-[4-[2-(4-fluorophenyl)ethenyl]phenyl]-4,5-dihydrooxazoleYield 41%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

The compound of Example 2 (0.7 g, 1.8 mmol), 4-fluorostyrene (1 g, 2.6 mmol), palladium acetate (0.03 g, 0.013 mmol) and tri-o-tolyphosphine (0.03 g, 0.01 mmol) were heated to 100°-120° C. in dimethylformamide (20 mL). After 3 h, palladium acetate (0.03 g, 0.013 mmol) was added and heating was continued for 2 h. The cooled reaction mixture was extracted with diethylether (50 mL) and water (100 mL). The diethylether solution was dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to chromatography on silica gel using hexanes/ethyl acetate (6:1) as eluent. The product was isolated as a solid (0.28 g): m.p.: 154°-156° C. 1H NMR (CDCl3, 200 MHz) δ 7.5-7.0 (m,13H), 5.5 (m,1H), 4.8 (m,1H), 4.3 (m,1H).

Workup

  1. temperatureheating
  2. waitwas continued for 2 h
  3. customThe cooled reaction mixture
  4. extractionwas extracted with diethylether (50 mL) and water (100 mL)
  5. dry with materialThe diethylether solution was dried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7f814d81edb44ce7a68f7711d864da05
Source dataset
uspto-grants-1998_06
Patent number
US05767281

Reaction notes

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