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

HRID 563786

Reaction equation

HRID 563786 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-81d61cfb8f294986860eb236a730ea7e
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Linked notes

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