Phosphorus tribromide → 1-(Bromomethyl)-2,5-dimethoxy-3,4,6-trimethylbenzene

HRID 232073Notes

Reaction equation

HRID 232073 reaction equation
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([O:13][CH3:14])=[C:7]([CH3:15])[C:4]=1[CH2:5]O.P(Br)(Br)[Br:17]>O1CCCC1.O>[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([O:13][CH3:14])=[C:7]([CH3:15])[C:4]=1[CH2:5][Br:17]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 13389492(2,5-Dimethoxy-3,4,6-trimethylphenyl)methanol

Product 1

HCID 142777601-(Bromomethyl)-2,5-dimethoxy-3,4,6-trimethylbenzeneYield 119.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 16.5 g (78.5 mmol) of 2,5-dimethoxy-3,4,6-trimethylbenzylalcohol in 90 ml of tetrahydrofuran was cooled to 0° C., to which 14.2 g (52.5 mmol) of phosphorus tribromide was added with stirring. After stirring at the same temperature for 30 minutes, the reaction mixture was diluted with water and extracted with isopropyl ether. The extract was washed with a saturated aqueous solution of sodium hydrogen carbonate and dried, from which the solvent was evaporated off. The residue was crystallized from methanol, to give 17.2 g (80.0%) of 2,5-dimethoxy-3,4,6-trimethylbenzyl bromide. m.p. 71°-72° C.

Workup

  1. additionwas added
  2. stirringAfter stirring at the same temperature for 30 minutes
  3. extractionextracted with isopropyl ether
  4. washThe extract was washed with a saturated aqueous solution of sodium hydrogen carbonate
  5. customdried, from which the solvent
  6. customwas evaporated off
  7. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-23d2ad97501547848d53227d39bb3277
Source dataset
uspto-grants-1989_07
Patent number
US04851413

Reaction notes

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