Phosphorus tribromide → 2-(Bromomethyl)-1,3-dichloro-5-methoxybenzene

HRID 1497501Notes

Reaction equation

HRID 1497501 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[CH2:11]O.P(Br)(Br)[Br:14].C(=O)([O-])O.[Na+]>O1CCCC1>[Br:14][CH2:11][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH3:9])=[CH:5][C:4]=1[Cl:10]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 14484725(2,6-Dichloro-4-methoxyphenyl)methanol

Product 1

HCID 592994792-(Bromomethyl)-1,3-dichloro-5-methoxybenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2,6-dichloro-4-methoxyphenyl)methanol (4.66 g) in tetrahydrofuran (50.0 mL) was added phosphorus tribromide (0.846 mL) under ice-cooling, followed by stirring for 1 hour under ice-cooling. To the reaction suspension was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to obtain 2-(bromomethyl)-1,3-dichloro-5-methoxybenzene (5.45 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-28daef647c424d1191d8fd797efc003f
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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