Phosphorus tribromide → HCID 22506886, compound
Reaction equation
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH3:13])=[C:7]([CH3:14])[C:4]=1[CH2:5]O.P(Br)(Br)[Br:16]>C1COCC1>[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH3:13])=[C:7]([CH3:14])[C:4]=1[CH2:5][Br:16]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2,5-dimethoxy-3,6-dimethylbenzyl alcohol (23.6 g, 0.12 mol) in THF (250 ml) was added dropwise phosphorus tribromide (5.7 ml, 0.06 mol) at 0° C., the mixture was stirred at room temperature for 2 hours, and then the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate (250 ml), and washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain 32.4 g of 2,5-dimethoxy-3,6-dimethylbenzyl bromide. The resultant bromide was dissolved in acetonitrile (50 ml) and added dropwise to a solution of sodium cyanide (7.35 g, 150 mmol) in water (75 ml) and acetonitrile (75 ml), and the mixture was stirred at room temperature for 3 days. The organic layer was separated, washed with saturated brine, and dried over magnesium sulfate. It was purified by silica gel chromatography with a small amount of silica gel and eluted with ethyl acetate, and the solvent was removed under reduced pressure. The residue was suspended in hexane, and crystals were filtered to obtain 23.5 g of the title compound.
Workup
- customthe solvent was removed under reduced pressure
- additionThe residue was diluted with ethyl acetate (250 ml)
- washwashed with a saturated aqueous solution of sodium bicarbonate
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-2ea8db1bd1964ea388f5f1a8d0bd8967
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06872718B1
Reaction notes
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