Thionyl Chloride → 3-phenoxybenzyl(1R)cis-2,2-dimethyl-3-(2,2-dibromovinyl)cyclopropane carboxylate

HRID 358115Notes

Reaction equation

HRID 358115 reaction equation
[CH3:1][C:2]1([CH3:12])[C@@H:4]([CH:5]=[C:6]([Br:8])[Br:7])[C@H:3]1[C:9]([OH:11])=[O:10].S(Cl)(Cl)=O.[O:17]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>N1C=CC=CC=1.C1C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[C@@H:4]([CH:5]=[C:6]([Br:8])[Br:7])[C@H:3]1[C:9]([O:11][CH2:27][C:26]1[CH:29]=[CH:30][CH:31]=[C:24]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:25]=1)=[O:10]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 262953-Phenoxybenzyl alcoholHCID 10924480Deltamethrinic acid

Product 1

HCID 130647753-phenoxybenzyl(1R)cis-2,2-dimethyl-3-(2,2-dibromovinyl)cyclopropane carboxylate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent2×

Procedure

The carboxylic acid described above was converted to its acid chloride by reaction with thionyl chloride in pyridine as described in Example 17 and the resulting acid chloride reacted with 3-phenoxybenzyl alcohol in dry benzene in the presence of pyridine as described in Example 17 to give 3-phenoxybenzyl(1R)cis-2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane carboxylate, m.p. 93°, nD 1.5848 (Compound P29A).

Sources & evidence

ORD record
ord-f92afa2f514f4cb29efda5ba026b71a6
Source dataset
uspto-grants-1984_08
Patent number
US04464391

Reaction notes

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