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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 908526Generated: October 25, 2026

Carbon tetrabromide → 1,3-Dioxane, 5-(2-bromoethyl)-2,2-dimethyl-

https://huagongshe.com/reaction/908526

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCarbon tetrabromideHCID 11205—
ReactantTriphenylphosphineHCID 11776—
ReactantSodium BicarbonateHCID 516892—
Reactant2-(2,2-Dimethyl-1,3-dioxan-5-yl)ethanolHCID 11816011—
SolventDimethylformamideHCID 6228—
Product1,3-Dioxane, 5-(2-bromoethyl)-2,2-dimethyl-HCID 178988—

Reaction Conditions

Temperature0 °C

Reaction Steps

To a solution of compound 32 (84 g, 0.528 mol) in dry DMF (500 mL) was added triphenylphosphine (207 g, 0.79 mol) with vigorous stirring until it becomes a clear solution. The mixture was cooled to 0° C. and added CBr4 (260 g, 0.79 mol) portion wise over a period of 30 min and allowed to stir at RT for 5 h. The reaction mixture was cooled to 0° C., added saturated NaHCO3 solution (200 mL) and extracted with hexane (4×200 mL). The combined organic layer was dried, concentrated under vacuum and the crude title compound (117 g) was used for next reaction without any purification. TLC: Pet. ether/EtOAc, 7:3, Rf=0.6

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08017620B2
Source datasetuspto-grants-2011_09
ORD IDord-8a9400e2ee204391b432642c46834d37
Source noteuspto-grants-2011_09