Triethylamine → 3-Bromo-4-fluorobenzyl methanesulfonate

HRID 2390116Notes

Reaction equation

HRID 2390116 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][OH:6].[CH3:11][S:12](Cl)(=[O:14])=[O:13].C(N(CC)CC)C>C(Cl)Cl>[CH3:11][S:12]([O:6][CH2:5][C:4]1[CH:7]=[CH:8][C:9]([F:10])=[C:2]([Br:1])[CH:3]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27733513-Bromo-4-fluorobenzyl Alcohol

Product 1

HCID 598548133-Bromo-4-fluorobenzyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A cooled (−20° C.) solution of 3-bromo-4-fluorobenzyl alcohol (Oakwood; 500 mg; 2.44 mmol) and methanesulfonyl chloride (123 μL; 1.59 mmol) in DCM (5 mL) was treated with a solution of triethylamine (255 μL; 1.83 mmol) in DCM (2.5 mL). The reaction mixture was allowed to warm to RT and stirred for 30 minutes before being quenched with water. The phases were separated and 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 colorless liquid.

Workup

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

Sources & evidence

ORD record
ord-c81fab0741c24032a7d8ac0253f69aaf
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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