3-(2,2-Dibromoethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride → HCID 20032126, compound

HRID 231840Notes

Reaction equation

HRID 231840 reaction equation
C(N1C2[C:7](=[CH:8][CH:9]=CC=2)[C:6]([CH:13]([OH:15])[CH3:14])=[C:5]1[C:16](F)(F)F)C#C.[Br:20][C:21]([Br:31])=[CH:22][CH:23]1[CH:25]([C:26](Cl)=[O:27])[C:24]1(C)C>N1C=CC=CC=1>[CH3:16][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH:22]([O:15][CH:13]([CH3:6])[CH3:14])([CH3:23])[CH3:21].[Br:31][C:21]([Br:20])=[CH:22][CH:23]1[CH:25]([C:26]([O-:27])=[O:15])[CH2:24]1

Participants

5

Reactant 2

HCID 129405823-(2,2-Dibromoethenyl)-2,2-dimethylcyclopropane-1-carbonyl chlorideHCID 88619781(RS) [1-(2-propynyl)-2-trifluoromethyl-(1H)-indol-3-yl]-ethanol

Product 2

HCID 20032126HCID 20032126, compoundHCID 21881879Diisopropylether hexane

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.82 g of 1 (RS) [1-(2-propynyl)-2-trifluoromethyl-(1H)-indol-3-yl]-ethanol and 20 ml of 3-(2,2-dibromoethenyl)-2,2-dimethyl-cyclopropane-carboxylic acid chloride were mixed together at ambient temperature under an inert atmosphere, and 0.3 ml of pyridine were added. After stirring for 18 hours, the solvents were evaporated under reduced pressure to obtain 3.15 g of crude product which was purified by chromatography over silica (eluent: hexane-ethyl acetate 9-1 then hexane-isopropyl ether 9-1) to obtain 1(RS) [1-(2-propynyl)-2-trifluoromethyl-)1H)-indol-3-yl]-ethyl 1R,cis 2,2-dimethyl [3-(2,2-dibromoethenyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =-30.5°±1.6° (c=0.6% in toluene).

Workup

  1. additionwere added
  2. customthe solvents were evaporated under reduced pressure
  3. customto obtain 3.15 g of crude product which
  4. customwas purified by chromatography over silica (eluent

Sources & evidence

ORD record
ord-0eb7d25190ac4e4fb8a88d52d2ed4394
Source dataset
uspto-grants-1989_07
Patent number
US04849443

Reaction notes

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