Ammonium Chloride → HCID 19931780, compound

HRID 21457Notes

Reaction equation

HRID 21457 reaction equation
C([Li])CCC.Br[C:7]#[C:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1[S:19][CH3:20].BrC(Br)=CC1C=CC(C(F)(F)F)=CC=1SC.[CH:37]1([C:40](Cl)=[O:41])[CH2:39][CH2:38]1.[Cl-].[NH4+]>C1COCC1>[CH:37]1([C:40](=[O:41])[C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=2[S:19][CH3:20])[CH2:39][CH2:38]1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 77637Cyclopropanecarbonyl chlorideHCID 199317581,1-Dibromo-2-[2-(methylsulphenyl)4-trifluoromethylphenyl]etheneHCID 19931787HCID 19931787, compoundHCID 178418339Butyllithium

Product 1

HCID 19931780HCID 19931780, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (2.5M, 1.45 ml) was added to a stirred cooled solution of 1-bromo-2-[2-(methylsulphenyl)-4-trifluoromethylphenyl]acetylene and 1,1-dibromo-2-[2-(methylsulphenyl)-4-trifluoromethylphenyl]ethene (1.0 g) in THF, maintaining the temperature below -70° C. The mixture was stirred for 30 minutes and cyclopropanecarbonyl chloride (0.75 g) was added. The temperature was allowed to rise to room temperature and the mixture was stirred for 2 hours, aqueous ammonium chloride was added and the mixture was extracted with ether, dried (MgSO4) and filtered. The flitrate was evaporated to dryness and the residue was purified by chromotography eluted with a mixture of hexane and ether to give 3-cyclopropyl-1-[2-(methylsulphenyl)-4-trifluoromethylphenyl]prop-1-yn-3-one (0.64 g) as yellow oil, NMR (CDCI3) 1.15(m,2H), 1.45(m,2H), 2.2(m,1H), 2.6(s,1H), 7.35(d,1H) 7.4(s,1H), 7.6(d,1H).

Workup

  1. temperaturemaintaining the temperature below -70° C
  2. customto rise to room temperature
  3. stirringthe mixture was stirred for 2 hours
  4. extractionthe mixture was extracted with ether
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe flitrate was evaporated to dryness
  8. customthe residue was purified by chromotography
  9. washeluted with a mixture of hexane and ether

Sources & evidence

ORD record
ord-8f520fa22393427582a68c87a0a28429
Source dataset
uspto-grants-1995_06
Patent number
US05424276

Reaction notes

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