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

HRID 599795Notes

Reaction equation

HRID 599795 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 three-necked bottle (250 ml); dissolving phosphorus tribromide (6.73 ml, 70.89 mmol) in dichlormethane (25 ml) for it to react at room temperature for 50 minutes, cooling in refrigeratory, slowly adding deionized water (18 ml, 1.0 mol) dropwise to quench, washing with deionized water (100 ml) twice, drying with anhydrous magnesium sulfate, filtering, washing the filter residue with dichlormethane (20 ml), conflating the filtrate, concentrating in rotarory evaporater, and vacuum drying to get 3,4,5-trimethoxyl benzyl bromine (16.05 g of faint yellow solid), yield: 84.44%.

Workup

  1. temperaturecooling in refrigeratory,
  2. customto quench
  3. washwashing with deionized water (100 ml) twice
  4. dry with materialdrying with anhydrous magnesium sulfate
  5. filtrationfiltering
  6. washwashing the filter residue with dichlormethane (20 ml)
  7. concentrationconcentrating in rotarory evaporater, and vacuum
  8. customdrying

Sources & evidence

ORD record
ord-4f37dd3764f74a11a1f60302287f661d
Source dataset
uspto-grants-2011_03
Patent number
US07897820B2

Reaction notes

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