Phosphorus tribromide → 4-Bromo-2-(bromomethyl)-1-fluorobenzene

HRID 1810543Notes

Reaction equation

HRID 1810543 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH2:8]O)[CH:7]=1.P(Br)(Br)[Br:12].C([O-])(O)=O.[Na+]>COCCOC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH2:8][Br:12])[CH:7]=1

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 2773352(5-Bromo-2-fluorophenyl)methanol

Product 1

HCID 135532954-Bromo-2-(bromomethyl)-1-fluorobenzene

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To (5-bromo-2-fluoro-phenyl)-methanol (1.2 g, 5.9 mmol) in DME (20 mL) was added phosphorus tribromide (0.83 mL, 8.8 mmol), and the reaction was stirred at room temperature for 6 hours. The mixture was cooled to 0° C. and adjusted to pH 6 with saturated aqueous NaHCO3. The solution was extracted with EtOAc, and the combined organic layers were dried, concentrated, and purified by silica gel chromatography to give the title compound.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionThe solution was extracted with EtOAc
  3. customthe combined organic layers were dried
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-a9cc92ff13174c8abf5c1a612cf3f2f7
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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