Phosphorus tribromide → 2-(Bromomethyl)-1-chloro-3-methoxybenzene

HRID 1946316Notes

Reaction equation

HRID 1946316 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH2:10]O.P(Br)(Br)[Br:13].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:9][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:10][Br:13]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 28945846HCID 28945846, compound

Product 1

HCID 223274432-(Bromomethyl)-1-chloro-3-methoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

[2-Chloro-6-(methyloxy)phenyl]methanol (0.224 g, 1.30 mmol) in dry dichloromethane (4.5 ml) under nitrogen was stirred and cooled to −10° C. A solution of phosphorus tribromide (0.357 g, 1.32 mmol, Aldrich) in dry dichloromethane (4.5 ml) was added dropwise over about 40 min. The reaction temperature was slowly allowed to warm to 5° C. over about six hours then cooled to 0° C. and saturated aqueous sodium bicarbonate (5 ml) was added. The layers were separated and the aqueous phase further extracted with chloroform. The combined organic extract was dried with magnesium sulphate, filtered and solvent evaporated in vacuo to give the title compound as a slightly yellow solid (0.232 g); LCMS: (System 4) tRET=3.07 min (no MH+ detected).

Workup

  1. temperatureto warm to 5° C. over about six hours
  2. temperaturethen cooled to 0° C.
  3. customThe layers were separated
  4. extractionthe aqueous phase further extracted with chloroform
  5. extractionThe combined organic extract
  6. dry with materialwas dried with magnesium sulphate
  7. filtrationfiltered
  8. customsolvent evaporated in vacuo

Sources & evidence

ORD record
ord-7568c16489224aa2986e36484dfa902c
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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