Phosphorus tribromide → 1-Bromo-2-(bromomethyl)-4-(trifluoromethyl)benzene

HRID 2064511Notes

Reaction equation

HRID 2064511 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH2:12]O.[Br:14]P(Br)Br.C([O-])(O)=O.[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH2:12][Br:14]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 27562482-Bromo-5-(trifluoromethyl)benzyl alcohol

Product 1

HCID 27562491-Bromo-2-(bromomethyl)-4-(trifluoromethyl)benzeneYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-bromo-5-(trifluoromethyl)phenyl)methanol (1.6 g, 6.27 mmol) in dichloromethane (10 mL) at 0° C. was added tribromophosphine (1.698 g, 6.27 mmol) over 2 hours. To the reaction mixture was added saturated NaHCO3 and the organic layers was separated, dried with NaSO4, filtered, and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% EtOAc in hexane) to afford the title compound (1.2 g, 3.77 mmol, 60.2% yield). 1H NMR (300 MHz, CDCl3) δ ppm 4.60 (s, 2H) 7.53-7.61 (m, 2H) 7.84 (s, 1H).

Workup

  1. customthe organic layers was separated
  2. dry with materialdried with NaSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-af2b893a60114019b580ad2cc882f872
Source dataset
uspto-grants-2012_10
Patent number
US08288428B2

Reaction notes

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