Phosphorus tribromide → 2-Bromomethyl-1,3-dichloro-4-methoxy-benzene

HRID 2235211Notes

Reaction equation

HRID 2235211 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([Cl:10])[C:3]=1[CH2:11]O.P(Br)(Br)[Br:14]>C(Cl)Cl>[Br:14][CH2:11][C:3]1[C:2]([Cl:1])=[C:7]([O:8][CH3:9])[CH:6]=[CH:5][C:4]=1[Cl:10]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 21980844(2,6-Dichloro-3-methoxyphenyl)methanol

Product 1

HCID 592995152-Bromomethyl-1,3-dichloro-4-methoxy-benzeneYield 112.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve (2,6-dichloro-3-methoxy-phenyl)-methanol (9.43 g, 45.5 mmol) in methylene chloride (180 ml) cool to 0° and add phosphorus tribromide (1.0M, 23 ml, 23 mmol) dropwise. Stir for 10 minutes at 0°, dilute with methylene chloride, quench with saturated aqueous sodium bicarbonate, separate layers, wash organic with water, brine dry over sodium sulfate, filter and concentrate to yield 7 g (57%) of the title compound: NMR (CDCl3) δ 7.28 (d, 1H), 6.85 (d, 1H), 4.77 (s, 2H), 3.90 (s, 3H).

Workup

  1. temperaturecool to 0°
  2. customquench with saturated aqueous sodium bicarbonate
  3. customseparate layers
  4. washwash organic with water, brine
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-cbef151c5f774ed692a952346e03f5d5
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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