Water → 2-(Bromomethyl)-1,4-dimethoxybenzene

HRID 2242348Notes

Reaction equation

HRID 2242348 reaction equation
P(Br)(Br)[Br:2].[CH3:5][O:6][C:7]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:8]=1[CH2:9]O.O>C(Cl)Cl>[Br:2][CH2:9][C:8]1[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:7]=1[O:6][CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 1184952,5-Dimethoxybenzyl alcohol

Product 1

HCID 5920212-(Bromomethyl)-1,4-dimethoxybenzeneYield 173.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of phosphorous tribromide (5.74 ml, 60.4 mmol) in anhydrous DCM (90 ml) was added over 20 min to a cooled, stirred solution of 2,5-dimethoxybenzyl alcohol (25.0 g, 148.8 mmol) in DCM (180 ml), maintaining the temperature between −5° C. and 0° C. Following the addition, the reaction was stirred at this temperature for a further 20 min. when water (200 ml) was added. After separation of the layers, the organic was washed with water (3×200 ml), dried with magnesium sulfate and evaporated to dryness under reduced pressure. The resulting crude product was crystallised from diethyl ether/heptane to afford 2-bromomethyl-1,4-dimethoxy-benzene (24.2 g, 72%).

Workup

  1. temperaturemaintaining the temperature between −5° C. and 0° C
  2. additionthe addition
  3. additionwas added
  4. customAfter separation of the layers
  5. washthe organic was washed with water (3×200 ml)
  6. dry with materialdried with magnesium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customThe resulting crude product was crystallised from diethyl ether/heptane

Sources & evidence

ORD record
ord-72b6a3a3a42241ef9a105a98bd6dc711
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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