Hydrochloric Acid → (2-phenoxy-4-thiazolyl)-methyl (1R,3R)2,2-dimethyl-3-(2,2-dibromoethenyl)-cyclopropane-1-carboxylate

HRID 544428Notes

Reaction equation

N1C=CC=CC=1.[CH3:7][C:8]1([CH3:18])[C@@H:10]([CH:11]=[C:12]([Br:14])[Br:13])[C@H:9]1[C:15](Cl)=[O:16].[O:19]([C:26]1[S:27][CH:28]=[C:29]([CH2:31][OH:32])[N:30]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>C1C=CC=CC=1>[CH3:7][C:8]1([CH3:18])[C@@H:10]([CH:11]=[C:12]([Br:14])[Br:13])[C@H:9]1[C:15]([O:32][CH2:31][C:29]1[N:30]=[C:26]([O:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[S:27][CH:28]=1)=[O:16]

Participants

Conditions

Temperature: 20 °C

Procedure

1.6 ml of pyridine was added dropwise at 0° C. to a solution of 1.7 g of (1R,3R) 2,2-dimethyl-3-[2,2-dibromoethenyl]-cyclopropane-1-carboxylicacid chloride and 1 g of the product of Step B in 20 ml of benzene and the mixture was stirred for 2 hours at 20° C. and was poured into aqueous N hydrochloric acid solution. The decanted organic phase was washed with water, dried and evaporated to dryness. The residue was chromatographed over silica gel and was eluted with a 9-1 hexane-ethyl acetate mixture to obtain 1.87 g of (2-phenoxy-4-thiazolyl)-methyl (1R,3R)2,2-dimethyl-3-(2,2-dibromoethenyl)-cyclopropane-1-carboxylate melting at ≃50° C. and having a specific rotation of [α]D20 =-9°±1° (c=1% in benzene).

Workup

washThe decanted organic phase was washed with water
customdried
customevaporated to dryness
customThe residue was chromatographed over silica gel
washwas eluted with a 9-1 hexane-ethyl acetate mixture

Sources & evidence

ORD record: ord-ea903fdccae940ff8c0c13b47091546d
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04450169

Reaction notes

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