Phosphorus tribromide → 1-(1-Bromoethyl)-3-fluorobenzene

HRID 911699Notes

Reaction equation

HRID 911699 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8](O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.P(Br)(Br)[Br:12]>C(Cl)(Cl)(Cl)Cl.ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]([Br:12])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 953483-Fluoro-alpha-methylbenzenemethanol

Product 1

HCID 156802311-(1-Bromoethyl)-3-fluorobenzeneYield 78.6%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve (±)-1-(3-fluorophenyl)ethanol (250 mg, 1.786 mmol) in carbon tetrachloride (10 mL). Add phosphorus tribromide (0.1 mL, 1.786 mmol) at 0° C. and stir the solution at room temperature overnight. Dilute the reaction mixture with dichloromethane and wash with brine. Dry the organic phase over Na2SO4, filter and concentrate in vacuo to obtain the title compound (285 mg) that was used without any further purification.

Workup

  1. washwash with brine
  2. dry with materialDry the organic phase over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f43f956977824dc49eca3a66313973de
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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