Phosphorus tribromide → 1-(Bromomethyl)-2,3,4-trimethoxybenzene

HRID 2351820Notes

Reaction equation

HRID 2351820 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([O:11][CH3:12])[C:4]=1[O:13][CH3:14].P(Br)(Br)[Br:16]>CCOCC>[CH3:14][O:13][C:4]1[C:5]([O:11][CH3:12])=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[CH2:2][Br:16]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 123571(2,3,4-Trimethoxyphenyl)methanol

Product 1

HCID 134493141-(Bromomethyl)-2,3,4-trimethoxybenzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 1-hydroxymethyl-2,3,4-trimethoxybenzene (1 g, 5 mmoles) in anhydrous ethered solution (10 ml) is injected into a three-necked flask supplied with a septum and equipped with a magnetic stirrer, which is swept with argon. Phosphorus tribromide at -20° C. (1.46 g, 5 mmoles) dissolved in ether (8 ml) is then added. The mixture is stirred at -10° C. for 2 hours and then washed with ice-cold water and finally with NaCl, and then dried over MgSO4. Evaporation at 0° C. under reduced pressure gives a colorless oil (1.24 g) which is homogeneous in TLC (Y=95%).

Workup

  1. customequipped with a magnetic stirrer
  2. additionis then added
  3. washwashed with ice-cold water and finally with NaCl
  4. dry with materialdried over MgSO4
  5. customEvaporation at 0° C. under reduced pressure

Sources & evidence

ORD record
ord-f66f91a2174f4055b4acdb1440c2fc1b
Source dataset
uspto-grants-1989_10
Patent number
US04873349

Reaction notes

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