(Diethylamino)sulfur trifluoride → 1-Bromo-4-(1-fluorocyclobutyl)benzene

HRID 2244315Notes

Reaction equation

HRID 2244315 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(S(F)(F)[F:19])CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([F:19])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 120954191-(4-Bromophenyl)cyclobutanol

Product 1

HCID 685641591-Bromo-4-(1-fluorocyclobutyl)benzeneYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5.66 g of 1-(4-bromophenyl)-cyclobutanol (24.92 mmol, described in example S2-A) in 70 ml DCM were added 4.23 g of (diethylamino)sulfur trifluoride (95%, 24.92 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 35 min, then sat. NaHCO3-solution was added and the resulting mixture was extracted with DCM. The combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to give a residue which was purified by flash column chromatography (100% pentane) to give 1-bromo-4-(1-fluoro-cyclobutyl)-benzene (3.66 g, 64%) as a colourless liquid.

Workup

  1. customat 0° C
  2. extractionthe resulting mixture was extracted with DCM
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a residue which
  8. customwas purified by flash column chromatography (100% pentane)

Sources & evidence

ORD record
ord-82e52bb77cfb4923aaf12191069461b6
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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