Benzene, 1-bromo-3-(trifluoromethyl)- → HCID 14009067, compound

HRID 1980625Notes

Reaction equation

HRID 1980625 reaction equation
[Mg].[F:2][C:3]([F:12])([F:11])[C:4]1[CH:5]=[C:6](Br)[CH:7]=[CH:8][CH:9]=1.[OH:13][C:14]1[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:15]=1[C:21](=[O:24])[CH2:22][CH3:23].[Cl-].[NH4+]>O1CCCC1>[F:2][C:3]([F:12])([F:11])[C:4]1[CH:5]=[C:6]([C:21]([C:15]2[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:14]=2[OH:13])([OH:24])[CH2:22][CH3:23])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 25517Ammonium ChlorideHCID 798562',4'-DihydroxypropiophenoneHCID 5462224Magnesium

Product 1

HCID 14009067HCID 14009067, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a Grignard reactant prepared from 14.6 g. of magnesium turnings and 135 g. of 3-trifluoromethylbromobenzene in 330 ml. of tetrahydrofurane a solution of 16.6 g. of 2',4'-dihydroxy-propiophenone in 83 ml. of tetrahydrofurane is added dropwise, at 50° C., and the mixture is stirred at this temperature for 30 additional minutes. After cooling, the reaction mixture is decomposed with a cold 20% aqueous ammonium chloride solution, with stirring. The phases are separated, the aqueous phase is extracted with tetrahydrofurane, the combined organic phases are washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent is distilled off in vacuo. The residue is decolored with activated carbon in methanol, the solvent is filtered off, and distilled off under reduced pressure. If desired, the product is crystallized from a mixture of ethyl acetate and n-hexane to yield 26.6 g. of the named compound, melting at 137° to 138° C.

Workup

  1. temperatureAfter cooling
  2. stirringwith stirring
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with tetrahydrofurane
  5. washthe combined organic phases are washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off in vacuo
  8. filtrationthe solvent is filtered off
  9. distillationdistilled off under reduced pressure
  10. customthe product is crystallized from a mixture of ethyl acetate and n-hexane
  11. customto yield 26.6 g

Sources & evidence

ORD record
ord-756ec93c585440fe93a7cfe0023ed4e0
Source dataset
uspto-grants-1985_04
Patent number
US04510338

Reaction notes

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