Water → methyl N-(5-bromomethyl-2-chlorobenzyl)carbamate

HRID 2414262Notes

Reaction equation

HRID 2414262 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][C:3]=1[CH2:4][NH:5][C:6](=[O:9])[O:7][CH3:8].P(Br)(Br)[Br:17].O.C(OCC)(=O)C>COCCOC>[Br:17][CH2:14][C:11]1[CH:12]=[CH:13][C:2]([Cl:1])=[C:3]([CH:10]=1)[CH2:4][NH:5][C:6](=[O:9])[O:7][CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24614Phosphorus tribromideHCID 22645125methyl N-(2-chloro-5-hydroxymethylbenzyl)carbamate

Product 1

HCID 22645123methyl N-(5-bromomethyl-2-chlorobenzyl)carbamateYield 209%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

6.2 g of methyl N-(2-chloro-5-hydroxymethylbenzyl)carbamate was dissolved in 50 ml of ethylene glycol dimethyl ether, and 2.7 g of phosphorus tribromide was dropwise added to this solution at −20° C., followed by stirring at room temperature for 1 hour. After completion of the reaction, water was added to the reaction solution, extraction with ethyl acetate was carried out, followed by washing with an aqueous sodium hydrogencarbonate solution, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 6.1 g of methyl N-(5-bromomethyl-2-chlorobenzyl)carbamate as white crystals.

Workup

  1. washby washing with an aqueous sodium hydrogencarbonate solution
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-37e4f85fd98944f39e6f909f7c23875f
Source dataset
uspto-grants-2004_11
Patent number
US06812229B1

Reaction notes

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