Phosphorus tribromide → [3-(2-Bromomethyl-4-nitro-phenoxy)-5-chloro-phenyl]-acetic acid methyl ester

HRID 656756Notes

Reaction equation

HRID 656756 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[CH2:21]O)[CH:8]=[C:7]([Cl:23])[CH:6]=1.P(Br)(Br)[Br:26]>COCCOC>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:6]=[C:7]([Cl:23])[CH:8]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[CH2:21][Br:26])[CH:10]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 58372735[3-Chloro-5-(2-hydroxymethyl-4-nitro-phenoxy)-phenyl]-acetic acid methyl ester

Product 1

HCID 58372722[3-(2-Bromomethyl-4-nitro-phenoxy)-5-chloro-phenyl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of [3-chloro-5-(2-hydroxymethyl-4-nitro-phenoxy)-phenyl]-acetic acid methyl ester (2.4 g, 6.8 mmol) in DME (20 mL) was added phosphorus tribromide (0.97 mL, 10.2 mmol), and the reaction was stirred for 1 hour at room temperature. After work-up with EtOAc and H2O, the crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. customAfter work-up with EtOAc and H2O, the crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9eafab87d9d24752a90925c015b2883b
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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