Ammonium Chloride → HCID 19931780, compound

HRID 2380204Notes

Reaction equation

HRID 2380204 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 filtrate 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-3one (0.64 g) as yellow oil, NMR (CDCl3) 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 filtrate 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-1e7b134ce23c4b3c9ecb23db5d062114
Source dataset
uspto-grants-1994_11
Patent number
US05366957

Reaction notes

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