Benzene, 1-bromo-2-(trifluoromethyl)- → HCID 9899486, compound

HRID 1591502Notes

Reaction equation

HRID 1591502 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([Sn](C)(C)C)=[CH:4][CH:3]=1.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:22])([F:21])[F:20]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:20][C:19]([F:22])([F:21])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 9806Benzene, 1-bromo-2-(trifluoromethyl)-HCID 617834Stannane, trimethyl(4-methylphenyl)-

Product 1

HCID 9899486HCID 9899486, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of 388 mg (1.52 mmol,1.4 eq.) of 4-methylphenyltrimethylstannane (Example 69, Step A) in 5 mL of toluene under a nitrogen atmosphere was treated with 238 mg of 2-bromobenzotrifluoride (1.06 mmol) and 64 mg of tetrakis(triphenylphosphine) palladium(0) and the resulting solution heated at reflux for 14 hours. The mixture was cooled, filtered and concentrated under vacuum to give an amber oil that was chromatographed on silica, eluting with hexane, to give the product. 1H NMR (300 MHz,CDCl3): 2.41 (s,3H), 7.2-7.8 (m,8H). EI-MS: calculated for C14H11F3 236; found 236 (M+,100%).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for 14 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give an amber oil that
  7. customwas chromatographed on silica
  8. washeluting with hexane
  9. customto give the product

Sources & evidence

ORD record
ord-9c02a613a35a4deaa8de7d6ce48d66c8
Source dataset
uspto-grants-1993_04
Patent number
US05206235

Reaction notes

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