Hydrochloric Acid → HCID 13504101, compound

HRID 1789338Notes

Reaction equation

HRID 1789338 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1.[Mg].II.[N:16]1([CH:21]([CH3:26])[C:22]([O:24]C)=O)[CH:20]=[CH:19][CH:18]=[N:17]1.Cl>O1CCCC1.O>[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:22]([C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:11])[F:12])=[CH:9][CH:8]=2)([OH:24])[CH:21]([N:16]2[CH:20]=[CH:19][CH:18]=[N:17]2)[CH3:26])=[CH:6][CH:5]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 5462224MagnesiumHCID 20041512Methyl 2-(1H-pyrazol-1-yl)propanoate

Product 1

HCID 13504101HCID 13504101, compoundYield 8.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4-trifluoromethoxybromobenzene (6.3 g.) in dry tetrahydrofuran (40 cm3) was added dropwise to a stirred mixture of magnesium turnings (0.62 g.), dry tetrahydrofuran (10 cm3) and a crystal of iodine under a nitrogen atmosphere. The reaction commenced after about 3 cm3 of the solution had been added and the mixture was warmed gently for a few minutes. When the addition was complete the mixture was stirred for 2 hours after which a solution of methyl 2-(1H-pyrazol-1-yl)propionate (2.0 g) in dry tetrahydrofuran (5.0 cm3) was added dropwise and the mixture then stirred for a further 2 hours at the ambient temperature. Finally the mixture was warmed to 40° C. to complete the reaction. The mixture was poured into water, acidified with dilute hydrochloric acid and extracted with two portions of diethyl ether 2×50 cm3. The extracts were combined, washed with water (3×50 cm3), dried over anhydrous magnesium sulphate and concentrated by removal of the solvent by evaporation under reduced pressure. The residual oil was subjected to purification by repeated chromatographic separation on a silica gel column eluted with a mixture of petroleum ether (boiling range 60°-80° C., 4 parts by volume) and ethyl acetate (1 part by volume) to yield 1,1-bis(4-trifluoromethoxyphenyl)-2-(1H-pyrazol-1-yl) propanol (500 mg.) as a pale yellow oil.

Workup

  1. additionhad been added
  2. temperaturethe mixture was warmed gently for a few minutes
  3. additionWhen the addition
  4. additionwas added dropwise
  5. temperatureFinally the mixture was warmed to 40° C.
  6. customthe reaction
  7. extractionextracted with two portions of diethyl ether 2×50 cm3
  8. washwashed with water (3×50 cm3)
  9. dry with materialdried over anhydrous magnesium sulphate
  10. concentrationconcentrated by removal of the solvent by evaporation under reduced pressure
  11. customThe residual oil was subjected to purification
  12. customseparation on a silica gel column
  13. washeluted with a mixture of petroleum ether (boiling range 60°-80° C., 4 parts by volume) and ethyl acetate (1 part by volume)

Sources & evidence

ORD record
ord-053fd1b6192942fb9e9834543cbccf19
Source dataset
uspto-grants-1987_08
Patent number
US04689337

Reaction notes

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