Phosphorus tribromide → [3-(2-Bromomethyl-4-methyl-phenoxy)-phenyl]-acetic acid ethyl ester

HRID 885240Notes

Reaction equation

HRID 885240 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=2[CH2:20]O)[CH:7]=1)[CH3:2].P(Br)(Br)[Br:24]>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=2[CH2:20][Br:24])[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 58237434[3-(2-Hydroxymethyl-4-methyl-phenoxy)-phenyl]-acetic acid ethyl ester

Product 1

HCID 58237502[3-(2-Bromomethyl-4-methyl-phenoxy)-phenyl]-acetic acid ethyl esterYield 48.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To [3-(2-hydroxymethyl-4-methyl-phenoxy)-phenyl]-acetic acid ethyl ester (0.17 g, 0.57 mmol) in 1,4-dioxane was added phosphorus tribromide (0.07 mL, 0.73 mmol), and the reaction was stirred for 1 hour at room temperature. After work-up, 0.1 g of the desired product was obtained.

Sources & evidence

ORD record
ord-657f036624254159995a9a5be6feb4af
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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