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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1429382Generated: November 1, 2026

Phosphorus tribromide → (R)-tert-Butyl(1-((2-(bromomethyl)benzyl)oxy)pent-4-en-2-yl)carbamate

https://huagongshe.com/reaction/1429382

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPhosphorus tribromideHCID 24614—
Reactant(R)-tert-Butyl(1((2-(hydroxymethyl)benzyl)oxy)pent-4-en-2-yl)carbamateHCID 68233280—
SolventCarbon TetrachlorideHCID 5943—
Product(R)-tert-Butyl(1-((2-(bromomethyl)benzyl)oxy)pent-4-en-2-yl)carbamateHCID 68233279161.9%

Reaction Conditions

Temperature0 °C

Reaction Steps

A solution of compound 18i (3.0 g, 9 mmol) in CCl4 (10 mL) was cooled in an ice bath. To this mixture was added PBr3 (1.0 g, 4.5 mmol) dropwise and the mixture was stirred at 0° C. for 2 hr. The mixture was quenched with water and extracted with DCM (3×50 mL). The combined organic layers were washed with brine and concentrated. The crude compound 18j (2.8 g, 80% yield) was used in the next step without purification. LCMS (m/z): 385.1 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08940722B2
Source datasetuspto-grants-2015_01
ORD IDord-20139ca545ec4ad38c55bb56853679a8
Source noteuspto-grants-2015_01