Phosphorus tribromide → HCID 23503539, compound

HRID 1835296Notes

Reaction equation

HRID 1835296 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9]O)=[CH:7][C:6]=1[O:13][CH3:14])[CH2:2][CH3:3].P(Br)(Br)[Br:16]>C(OCC)C>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][Br:16])=[CH:7][C:6]=1[O:13][CH3:14])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 2125298(3-Methoxy-4-propoxyphenyl)methanol

Product 1

HCID 23503539HCID 23503539, compoundYield 195.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 4-(propyloxy)-3-methoxybenzyl alcohol (2.28 g, 11.62 mmol) in anhydrous diethyl ether (30 mL) was slowly added PBr3 (0.55 mL, 5.81 mmol) via syringe, and the resulting mixture was stirred at room temperature for 2 hours. The mixture was diluted with diethyl ether (150 mL) and washed with saturated aqueous NaHCO3 (2×75 mL) and brine (2×75 mL). The organic layer was dried over anhydrous MgSO4, and the solvent was removed under reduced pressure to afford 4-(propyloxy)-3-methoxybenzyl bromide (2.94 g, 98%) as a white solid.

Workup

  1. washwashed with saturated aqueous NaHCO3 (2×75 mL) and brine (2×75 mL)
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bc60853cd40342579d250e72af56fc99
Source dataset
uspto-grants-2004_08
Patent number
US06770658B2

Reaction notes

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