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

HRID 885249
Notes
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Reaction equation

HRID 885249 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19]O)[CH:6]=1.P(Br)(Br)[Br:23].C([O-])(O)=O.[Na+]>COCCOC>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19][Br:23])[CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 58237523[3-(4-Bromo-2-hydroxymethyl-phenoxy)-phenyl]-acetic acid methyl ester

Product 1

HCID 58237479[3-(4-Bromo-2-bromomethyl-phenoxy)-phenyl]acetic acid methyl esterYield 85.2%

Reagents, catalysts & solvents 1

HCID 80711,2-Dimethoxyethane
Solvent

Procedure

To [3-(4-bromo-2-hydroxymethyl-phenoxy)-phenyl]-acetic acid methyl ester (3 g, 8.5 mmol) in DME (30 mL) under N2 was added phosphorus tribromide (1.2 mL, 12.8 mmol), and the reaction was stirred at room temperature for 6 hours. The solution was cooled to 0° C. and adjusted to pH 6 with saturated aqueous NaHCO3, and the mixture was extracted with EtOAc. The crude material was purified by silica gel chromatography to give the desired product as a colorless oil (3 g).

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. extractionthe mixture was extracted with EtOAc
  3. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-82243b7214c94865921dfb310eda662e
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08242145B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes