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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1468692Generated: October 31, 2026

Lithium Chloride → 7-Bromo-2-cyclopropyl-5-methyl-6-vinylbenzo[d]thiazole

https://huagongshe.com/reaction/1468692

Reaction equation

Participants

RoleNameHCIDCharge
ReactantLithium ChlorideHCID 433294—
ReactantTri(butyl)vinyltinHCID 53438229—
Reactant7-Bromo-2-cyclopropyl-5-methylbenzo[d]thiazol-6-yl trifluoromethanesulfonateHCID 89158213—
CatalystHCID 178418476HCID 178418476—
SolventDimethylformamideHCID 6228—
Product7-Bromo-2-cyclopropyl-5-methyl-6-vinylbenzo[d]thiazoleHCID 89157837—

Reaction Steps

To a solution of 7-bromo-2-cyclopropyl-5-methylbenzo[d]thiazol-6-yl trifluoromethanesulfonate (16) (410 mg, 0.988 mmol) in DMF (4 ml), was added tributylvinyltin (0.43 ml, 1.47 mmol), LiCl (125 mg, 2.94 mmol) and PdCl2(PPh3)2 (70 mg, 0.096 mmol). The reaction mixture was reacted at 80° C. overnight. The reaction was cooled down, washed by saturated NaHCO3 solution, extracted by EtOAc. The organic phase was combined, dry over MgSO4, filtered, concentrated and purified by silica gel column, eluting by 0-50% EtOAc in hexanes.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09006229B2
Source datasetuspto-grants-2015_04
ORD IDord-a96f2d525dde40f89ae1d5f04ecc9a59
Source noteuspto-grants-2015_04