Ammonium Chloride → HCID 53235736, compound

HRID 561507Notes

Reaction equation

HRID 561507 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[CH:13]([Mg]Br)=[CH2:14].[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]([OH:8])[CH:13]=[CH2:14])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 679964-(Trifluoromethyl)benzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 53235736HCID 53235736, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 75.0 g (431 mmol) of 4-(trifluoromethyl)benzaldehyde in 750 ml of diethyl ether was slowly added dropwise to 517 ml (517 mmol) of a 1N solution of vinylmagnesium bromide in tetrahydrofuran at RT under argon. After heating under reflux for 1 h, the reaction mixture was added to saturated aqueous ammonium chloride solution and extracted with tert-butyl methyl ether. The organic phase was dried, filtered and concentrated. The crude product was purified by column chromatography on silica gel (mobile phase: petroleum ether/ethyl acetate 9/1) to result in 87.0 g (100% of theory) of the title compound.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 1 h
  3. extractionextracted with tert-butyl methyl ether
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography on silica gel (mobile phase: petroleum ether/ethyl acetate 9/1)

Sources & evidence

ORD record
ord-f1c3ea3a32df4c7bbca2298d66487ce1
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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