Triethylamine → HCID 58522007, compound

HRID 2390120Notes

Reaction equation

HRID 2390120 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[F:10].[CH3:11][S:12](Cl)(=[O:14])=[O:13].C(N(CC)CC)C>C(Cl)Cl>[CH3:11][S:12]([O:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([F:10])[CH:4]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20682297(4-Bromo-3-fluorophenyl)methanol2×

Product 1

HCID 58522007HCID 58522007, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A cooled (0° C.) solution of (4-bromo-3-fluorophenyl)methanol (Intermediate 9; 299 mg; 1.46 mmol) and methanesulfonyl chloride (147 μL; 1.90 mmol) in DCM (3 mL) was treated slowly with a solution of triethylamine (305 μL; 2.19 mmol) in DCM (1.5 mL). The reaction mixture was allowed to warm to RT and stirred for 45 minutes before being quenched by addition of water. The organic phase was washed with HCl (0.1N in water) and brine, dried over MgSO4, filtered and concentrated to dryness affording a residue, which was purified by flash column chromatography, eluting with cyclohexane containing increasing amounts of EtOAc to give the title compound as a colourless liquid.

Workup

  1. custombefore being quenched by addition of water
  2. washThe organic phase was washed with HCl (0.1N in water) and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customaffording a residue, which
  7. customwas purified by flash column chromatography
  8. washeluting with cyclohexane containing
  9. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-2911f88e743d4fb1a85c91fe615fa43f
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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