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

HRID 1109658Notes

Reaction equation

HRID 1109658 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][CH2:14][CH2:15]O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].P(Br)(Br)[Br:18].O>O1CCCC1.C(OCC)(=O)C>[Br:18][CH2:15][CH2:14][CH2:13][C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 64288433-(3,4,5-Trimethoxyphenyl)Propan-1-Ol

Product 1

HCID 226096115-(3-Bromopropyl)-1,2,3-trimethoxybenzeneYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(3,4,5-trimethoxyphenyl)-propan-1-ol (9.50 g, 0.042 mol) in 50 ml of tetrahydrofuran, 5.0 ml (0.053 mol) of phosphorus tribromide were added dropwise at 0° C., followed by stirring at room temperature for 12 hours. The reaction mixture was added with water under ice cooling. The resulting solution was dissolved in 200 ml of ethyl acetate. The orqanic layer was washed successively with water, saturated NaHCO3 and saturated NaCl and then dried over anhydrous magnesium sulfate. The solvent was thereafter distilled off under reduced pressure. The oil thus obtained was purified by column chromatography (silica gel: "MERCK #9385", eluent: ether), whereby 10.2 g of the title compound were obtained as colorless oil (yield: 84%).

Workup

  1. washThe orqanic layer was washed successively with water, saturated NaHCO3 and saturated NaCl
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was thereafter distilled off under reduced pressure
  4. customThe oil thus obtained
  5. customwas purified by column chromatography (silica gel: "MERCK #9385", eluent: ether)

Sources & evidence

ORD record
ord-3d1b16a97d0447d782c6317784bbae8a
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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