Dabco → HCID 86737383, compound

HRID 1732638Notes

Reaction equation

HRID 1732638 reaction equation
[Cl:1][C:2]([C:12]([Cl:15])([F:14])[F:13])=[CH:3][C@H:4]1[C@H:6]([C:7]([OH:9])=[O:8])[C:5]1([CH3:11])[CH3:10].[OH-].[K+].Br[CH2:19][C:20]1[C:21]([Cl:33])=[C:22]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:24][C:25]=1[Cl:26].N12CCN(CC1)CC2>CCCCCCC.C(#N)C>[Cl:1][C:2]([C:12]([Cl:15])([F:13])[F:14])=[CH:3][C@@H:4]1[C@H:6]([C:7]([O:9][CH2:19][C:20]2[C:21]([Cl:33])=[C:22]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:23]=[CH:24][C:25]=2[Cl:26])=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 9237DabcoHCID 14797Potassium HydroxideHCID 203043003-(Bromomethyl)-2,4-dichloro-1,1'-biphenylHCID 86737384HCID 86737384, compound2×

Product 1

HCID 86737383HCID 86737383, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8900HeptaneSolvent

Procedure

This compound was prepared in the manner of Examples 8, 9, and 10 using 2.3 g (0.009 mole) of cis, trans-3-(2,3-dichloro-3,3-difluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid (compound 4.4, Table III), 0.6 g (0.009 mole) of potassium hydroxide, 2.8 g (0.009 mole) of 3-bromomethyl-2,4-dichloro[1,1'-biphenyl] and 0.1 g of 1,4-diazabicyclo[2.2.2]octane in 50 ml of heptane and 50 ml of acetonitrile. The crude product was purified by removing the volatiles by distillation using a Kugelrohr bulb to bulb distilling system at 130°-140° C./0.3-0.5 mm. The pot residue was subjected to column chromatography on silica gel, eluting with hexane, then 25:1-hexane:ethyl acetate. Appropriate fractions were combined and subjected to liquid chromatography using 66.6:1-hexane:ethyl acetate as the eluant. The appropriate fractions were combined to give 0.29 g of (2,4-dichloro[1,1'-biphenyl]-3-yl)methyl cis-3-(2,3-dichloro-3,3-difluoro- 1-propenyl)-2,2-dimethylcyclopropanecarboxylate. The nmr and ir spectra were consistent with the proposed structure.

Workup

  1. customThe crude product was purified
  2. customby removing the volatiles
  3. distillationby distillation
  4. distillationdistilling system at 130°-140° C./0.3-0.5 mm
  5. washeluting with hexane

Sources & evidence

ORD record
ord-667e178e70724e61971b5f1bff90471c
Source dataset
uspto-grants-1980_12
Patent number
US04238505

Reaction notes

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