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

HRID 240275

Reaction equation

HRID 240275 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9]O.P(Br)(Br)[Br:12]>COCCOC.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][Br:12]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 27733492-Bromo-5-fluorobenzyl alcohol

Product 1

HCID 5179721-Bromo-2-(bromomethyl)-4-fluorobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of (2-bromo-5-fluorophenyl)methanol (11, 4.10 g, 20.0 mmol) in dry DME (40 mL) at 0° C. was added a solution of PBr3 (3.25 g, 12.0 mmol) in dry DME (40 mL) dropwise. The mixture was then slowly warmed up to RT and stirred at for another 3 h. The mixture was diluted with water (100 mL), and extracted with 1:1 petroleum-ether-EtOAc (100 mL×2). The combined extracts were washed with saturated NaHCO3 and brine, dried over MgSO4 and concentrated to give 1-bromo-2-(bromomethyl)-4-fluorobenzene (12).

Workup

  1. extractionextracted with 1:1 petroleum-ether-EtOAc (100 mL×2)
  2. washThe combined extracts were washed with saturated NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e50fddf970314d75839db7765671e3e3
Source dataset
uspto-grants-2014_02
Patent number
US08648073B2

Linked notes

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