Pyridine → 4(2-chloroallyl)benzyl(1R)cis-3(2,2-dibromovinyl)-2,2-dimethylcyclopropane carboxylate

HRID 979540Notes

Reaction equation

HRID 979540 reaction equation
[Cl:1][C:2](=[CH2:12])[CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1.[Br:13][C:14]([Br:24])=[CH:15][C@H:16]1[C@@H:18]([C:19](Cl)=[O:20])[C:17]1([CH3:23])[CH3:22].N1C=CC=CC=1>C1C=CC=CC=1>[Br:13][C:14]([Br:24])=[CH:15][C@H:16]1[C@@H:18]([C:19]([O:9][CH2:8][C:7]2[CH:10]=[CH:11][C:4]([CH2:3][C:2]([Cl:1])=[CH2:12])=[CH:5][CH:6]=2)=[O:20])[C:17]1([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12940583Deltamethric Acid ChlorideHCID 132432854(2-Chloroallyl)benzyl alcohol

Product 1

HCID 132432944(2-chloroallyl)benzyl(1R)cis-3(2,2-dibromovinyl)-2,2-dimethylcyclopropane carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The alcohol of Example 2 (0.078 g) in benzene (2 ml) is added to (IR)cis 3-(2,2-dibromovinyl)2,2-dimethylcyclopropane carbonyl chloride (0.135 g) in benzene (3 ml). Pyridine (0.06 ml) is then added and the mixture stirred at 20° for 16 hours. This is chromatographed on florisil and the fraction eluted by 7% ether in petrol evaporated to a residue of 0.19 g (96%) ester, nD20 1.5692.

Workup

  1. customThis is chromatographed on florisil
  2. washthe fraction eluted by 7% ether in petrol
  3. customevaporated to a residue of 0.19 g (96%) ester

Sources & evidence

ORD record
ord-b89bed44f04d4f70a1ff54f40b5eb027
Source dataset
uspto-grants-1987_05
Patent number
US04668702

Reaction notes

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