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

HRID 1033448Notes

Reaction equation

HRID 1033448 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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[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(O) 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,3), 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-6479dacfaa8e4f9d9bff92f4760a428e
Source dataset
uspto-grants-1994_05
Patent number
US05310737

Reaction notes

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