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

HRID 1731565Notes

Reaction equation

HRID 1731565 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-5ab47a1063324138999265089cff042f
Source dataset
uspto-grants-1986_11
Patent number
US04622337

Reaction notes

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