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

HRID 1084481Notes

Reaction equation

HRID 1084481 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 thionylchloride 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-phenoxy-benzyl [1R-cis-]-2,2-dimethyl-3-(2,2-dibromovinyl)cyclopropane carboxylate, mp 93°, nD 1.5848 (Compound P29A).

Sources & evidence

ORD record
ord-ef557cb4b79b46858efdd9c3a75cf9a8
Source dataset
uspto-grants-1991_04
Patent number
US05004822

Reaction notes

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