Phosphorus tribromide → HCID 59712454, compound

HRID 2222447Notes

Reaction equation

HRID 2222447 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:18][CH3:19])=[C:7]([CH:17]=1)[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].P(Br)(Br)[Br:21]>C(COC)OC.CCOCC>[Br:21][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:18][CH3:19])=[C:7]([CH:17]=1)[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 59712518t-Butyl N-[5-(hydroxymethyl)-2-methoxybenzyl]carbamate

Product 1

HCID 59712454HCID 59712454, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

1.65 g of t-butyl N-[5-(hydroxymethyl)-2-methoxybenzyl]carbamate was dissolved in 20 ml of dimethoxyethane, 0.53 ml of phosphorus tribromide was added under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ether and washed with water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was subjected to silica gel column chromatography, to give 1.76 g of the title compound from the 3:1 hexane-ethyl acetate fraction.

Workup

  1. temperaturecooling
  2. washwashed with water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2f02276b95b5442e9bdc6ab4cffc4d29
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

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