Ammonium Chloride → HCID 18989441, compound

HRID 2395598Notes

Reaction equation

HRID 2395598 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[F:5][C:6]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:7]=1[CH:8]=[O:9].[NH4+].[Cl-]>C1COCC1>[CH:1]([CH:8]([C:7]1[CH:10]=[C:11]([C:14]([F:15])([F:16])[F:17])[CH:12]=[CH:13][C:6]=1[F:5])[OH:9])=[CH2:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 27349042-Fluoro-5-(trifluoromethyl)benzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 18989441HCID 18989441, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

52.6 ml (0.0526 mol) of a 1M solution of vinylmagnesium bromide in THF are added dropwise at a temperature below 25° C. to a solution of 10.1 g (0.0526 mol) of 2-fluoro-5-(trifluoromethyl)benzaldehyde (prepared according to Example P) in 53 ml of anhydrous THF. The mixture is then stirred for 2 h 30 at room temperature. Hydrolysis is carried out with a saturated aqueous NH4Cl solution while cooling between 10° and 20° C.; extraction is carried out with ether and the extract is washed with water, dried over Na2SO4, filtered and evaporated under vacuum. The residue is used without subsequent purification in the following stage. Yd.: 11.6 g (quantitative)

Workup

  1. customHydrolysis
  2. temperaturewhile cooling between 10° and 20° C.
  3. extractionextraction
  4. washthe extract is washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customThe residue is used without subsequent purification in the following stage

Sources & evidence

ORD record
ord-5fa542637ddf4743b0fe4747e0751a78
Source dataset
uspto-grants-1996_02
Patent number
US05489592

Reaction notes

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