Phosphorus tribromide → HCID 22506826, compound

HRID 985591Notes

Reaction equation

HRID 985591 reaction equation
[CH3:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:7]([CH:10]([CH3:12])[CH3:11])=[CH:8][CH:9]=1)[CH2:5]O.P(Br)(Br)[Br:16]>C1COCC1>[CH3:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:7]([CH:10]([CH3:12])[CH3:11])=[CH:8][CH:9]=1)[CH2:5][Br:16]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 69739073HCID 69739073, compound

Product 1

HCID 22506826HCID 22506826, compoundYield 211%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methyl-6-(1-methylethyl)-2-methoxybenzyl alcohol (15.9 g, 80 mmol) in THF (160 ml) was added phosphorus tribromide (3.80 ml, 40 mmol) at 0° C. and the mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to obtain 21.7 g of the title compound as an oil.

Workup

  1. washThe reaction mixture was washed with saturated brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-9e5ac4f81ce84162ba7658649510b8c5
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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