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

HRID 357704

Reaction equation

HRID 357704 reaction equation
[CH3:1][O:2][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.N1C=CC=CC=1.P(Br)(Br)[Br:22]>O1CCCC1>[CH3:1][O:2][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:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 774493,4,5-Trimethoxybenzyl alcohol

Product 1

HCID 103552715-(Bromomethyl)-1,2,3-trimethoxybenzeneYield 202.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3,4,5-trimethoxybenzyl alcohol (20.2 g, 0.108 mol) in 300 ml of dry tetrahydrofuran was added 4.12 ml (0.052 mol) of pyridine, and cooled to 0° C. A solution of phosphorous tribromide (4.8 ml, 0.051 mol) in 20 ml of dry tetrahydrofuran was added dropwise to the above solution at 0 ° C. The mixture was stirred for 1 hr. Tetrahydrofuran was concentrated. The residue was then diluted with 200 ml of 10% hydrochloric acid, and then extracted with 200 ml of ethyl acetate. The extract was dried over magnesium sulfate, filtered, concentrated, and dried in vacuum overnight. 3,4,5-Trimethoxybenzyl bromide (27 g, 100% yield) was obtained as a white solid, which can be used without further purification.

Workup

  1. concentrationTetrahydrofuran was concentrated
  2. additionThe residue was then diluted with 200 ml of 10% hydrochloric acid
  3. extractionextracted with 200 ml of ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried in vacuum overnight

Sources & evidence

ORD record
ord-d81fec49ae5444638cd057f3f55b7c37
Source dataset
uspto-grants-1998_11
Patent number
US05840991

Linked notes

Loading…