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

HRID 1875643Notes

Reaction equation

HRID 1875643 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=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:3]=[C:4]([O:8][CH2:12][CH2:11][CH2:10][Br:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 97433-FluorophenolHCID 10796Cesium carbonate

Product 1

HCID 232944331-(3-Bromopropoxy)-3-fluorobenzeneYield 13.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-fluorophenol (0.040 mL, 0.448 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (0.450 mL, 4.43 mmol) followed by Cs2CO3 (0.246 g, 0.756 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 (0.0137 g, 13.2%). ELMS Rt (2.28 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-ce574417d89945ff8ecdd9b27a5b16f0
Source dataset
uspto-grants-2012_11
Patent number
US08309572B2

Reaction notes

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