1,3-Dibromopropane → 1-(3-Bromopropoxy)-4-fluorobenzene

HRID 533847

Reaction equation

HRID 533847 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Br:9][CH2:10][CH2:11][CH2:12]Br.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:11][CH2:10][Br:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 97324-FluorophenolHCID 10796Cesium carbonate

Product 1

HCID 2600041-(3-Bromopropoxy)-4-fluorobenzeneYield 14.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-fluorophenol (0.0567 g, 0.506 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (0.520 mL, 5.12 mmol) followed by Cs2CO3 (0.252 g, 0.774 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (4 mL) and extracted with DCM (8 mL). The organic layer was dried through a phase separator and concentrated under vacuum. The residue was taken up in DMSO and purified by preparatory HPLC (without TFA) to give the title compound (0.0173 g, 14.7%). EI-MS Rt (2.25 min).

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe resulting residue was treated with H2O (4 mL)
  3. extractionextracted with DCM (8 mL)
  4. customThe organic layer was dried through a phase separator
  5. concentrationconcentrated under vacuum
  6. custompurified by preparatory HPLC (without TFA)

Sources & evidence

ORD record
ord-9d98d6e85aed4b43af87629715cfbacc
Source dataset
uspto-grants-2014_10
Patent number
US08853404B2

Linked notes

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