Water → 5-(Bromomethyl)-1,2,3-trimethoxybenzene

HRID 1867633Notes

Reaction equation

HRID 1867633 reaction equation
[O:1]([C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6]O)[CH3:2].P(Br)(Br)[Br:16].O>ClCCl>[O:1]([C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6][Br:16])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 774493,4,5-Trimethoxybenzyl alcohol

Product 1

HCID 103552715-(Bromomethyl)-1,2,3-trimethoxybenzeneYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolving 3,4,5-trimethoxyl benzyl alcohol (14.05 g, 70.89 mmol) in dichlormethane (100 ml) in a 250 ml three-necked flask; phosphorus tribromide (6.73 ml, 70.89 mmol) in dichlormethane (25 ml) was added dropwise and allowed to react at room temperature for 50 minutes, cooling in ice bath, slowly adding deionized water (18 ml, 1.0 mol) dropwise to quench the reaction, washing with deionized water (100 ml) twice, drying with anhydrous magnesium sulfate, filtering, washing the filter residue with dichlormethane (20 ml), the combined organic layer was concentrated in rotatory evaporater to dry, and was further dried under vacuum to afford 3,4,5-trimethoxyl benzyl bromide (16.05 g of faint yellow solid), yield 84.44%.

Workup

  1. customto react at room temperature for 50 minutes
  2. temperaturecooling in ice bath
  3. customto quench
  4. customthe reaction
  5. washwashing with deionized water (100 ml) twice
  6. dry with materialdrying with anhydrous magnesium sulfate
  7. filtrationfiltering
  8. washwashing the filter residue with dichlormethane (20 ml)
  9. concentrationthe combined organic layer was concentrated in rotatory evaporater
  10. customto dry
  11. customwas further dried under vacuum

Sources & evidence

ORD record
ord-361c5eefffc9426882449bb9c003a6cd
Source dataset
uspto-grants-2009_12
Patent number
US07632863B2

Reaction notes

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