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

HRID 19767Notes

Reaction equation

HRID 19767 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(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

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 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 colorless 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-8cb30b2a5fa74259aa6b20b955ff6ebf
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Reaction notes

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