Dichloromethane → 1-(1-Bromoethyl)-2,4,5-trifluorobenzene

HRID 1818968Notes

Reaction equation

HRID 1818968 reaction equation
P(Br)(Br)[Br:2].C(Cl)Cl.[F:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=1[CH:17](O)[CH3:18]>O>[Br:2][CH:17]([C:10]1[CH:11]=[C:12]([F:16])[C:13]([F:15])=[CH:14][C:9]=1[F:8])[CH3:18]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 24614Phosphorus tribromideHCID 67092124HCID 67092124, compound

Product 1

HCID 578858611-(1-Bromoethyl)-2,4,5-trifluorobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorus tribromide (0.275 mL) and anhydrous methylene chloride (12 mL) were combined and the solution cooled over ice water for 15 minutes. The solution was added to a mixture of 1-(2,4,5-trifluorophenyl)ethanol (0.506 g) and methylene chloride (8 mL), and the reaction was stirred at room temperature for 1.5 hours. The reaction mixture was then poured into H2O and extracted into methylene chloride. The organic phase was isolated, dried with magnesium sulfate, filtered and concentrated (without heat) to give the title compound. 1H-NMR (CD3OD, 400 MHz) δ 2.00 (3H, d, J=7.1 Hz), 5.37 (1H, m), 6.92 (1H, m), 7.36 (1H, m).

Workup

  1. extractionextracted into methylene chloride
  2. customThe organic phase was isolated
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. temperature(without heat)

Sources & evidence

ORD record
ord-12d47302c42d47bea892dce28bca818e
Source dataset
uspto-grants-2009_10
Patent number
US07601716B2

Reaction notes

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