Hydrochloric Acid → HCID 68681341, compound

HRID 1594342Notes

Reaction equation

HRID 1594342 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[Mg].[C:14]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)#N.[Cl-].[NH4+].Cl.C1C[O:28]CC1>>[F:10][C:9]([F:12])([F:11])[O:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[O:28])=[CH:3][CH:4]=1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 75064-CyanopyridineHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 5462224Magnesium

Product 1

HCID 68681341HCID 68681341, compound

Conditions

Temperature
40 °C

Procedure

To a Grignard Reagent prepared from 21.3 grams (0.088 mole) of 1-bromo-4-trifluoromethoxybenzene and 2.5 grams (0.102 gram-atom) of magnesium metal was added a solution of 7.1 grams (0.068 mole) of 4-cyanopyridine in 50 mL of THF. Upon completion of addition, the reaction mixture was stirred at 40° C. for 18 hours. After this time, the reaction mixture was poured into an aqueous dilute solution of ammonium chloride, and was acidified to a pH of 3 with aqueous 10% hydrochloric acid. The mixture was extracted with methylene chloride and the combined extracts were dried with sodium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using acetone, methylene chloride, and mixtures thereof as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. extractionThe mixture was extracted with methylene chloride
  3. dry with materialthe combined extracts were dried with sodium sulfate
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure to a residue
  6. customThe residue was purified with column chromatography on silica gel
  7. concentrationconcentrated under reduced pressure
  8. customyielding the subject compound

Sources & evidence

ORD record
ord-000b6ed2dbbd43f5a02505a2304be97f
Source dataset
uspto-grants-2007_11
Patent number
US07300946B2

Reaction notes

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