Phosphorus tribromide → 1-(Bromomethyl)-2,3,4,5-tetramethoxy-6-methylbenzene

HRID 2268491Notes

Reaction equation

HRID 2268491 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[C:6]([O:13][CH3:14])=[C:5]([CH3:15])[C:4]=1[CH2:16]O.P(Br)(Br)[Br:19]>C1COCC1>[Br:19][CH2:16][C:4]1[C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[C:7]([O:11][CH3:12])=[C:6]([O:13][CH3:14])[C:5]=1[CH3:15]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 183485582,3,4,5-Tetramethoxy-6-methylphenylmethanol

Product 1

HCID 148523231-(Bromomethyl)-2,3,4,5-tetramethoxy-6-methylbenzeneYield 161.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3,4,5-tetramethoxy-6-methylphenylmethanol (44.4 g) in THF (200 ml) was dropwise added phosphorus tribromide (29.8 g) with cooling with ice. After being stirred for 1 hr, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo to yield the entitled compound (54.4 g) as an oil.

Workup

  1. temperaturewith cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride
  4. customdried
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3d886d2305e64f8780937ea823db3818
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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