Pyridine → HCID 15364878, compound

HRID 387630Notes

Reaction equation

HRID 387630 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].N1C=CC=CC=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(=O)([O-])O.[Na+]>ClCCl>[CH3:17][S:18]([O:10][CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 27340892-(2-Bromophenyl)ethan-1-ol

Product 1

HCID 15364878HCID 15364878, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9.8 g of 2-(2-bromophenyl)ethanol and 4.7 cm3 of pyridine are dissolved under an inert atmosphere in 200 cm3 of dichloromethane at a temperature close to 20° C. The reaction mixture is cooled to a temperature close to 0° C. and 4.55 cm3 of methanesulfonyl chloride are introduced dropwise. The stirring is continued for 72 h, during which time the medium is allowed to gradually climb back up to a temperature close to 20° C. 100 cm3 of a saturated aqueous solution of sodium hydrogen carbonate are added to the reaction mixture. Stirring is continued for 10 min. The aqueous phase is extracted with dichloromethane. The organic phases are combined, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered then concentrated using a rotary evaporator under reduced pressure (5 kPa). The 18 g of brown oil obtained are purified by flash chromatography over silica (column: 200 g; particle size: 15-40 μm; eluent: 100% dichloromethane to 90% dichloromethane/10% ethyl acetate gradient). After concentrating the fractions under reduced pressure, 12.9 g of 2-(2-bromophenyl)ethyl methanesulfonate are obtained in the form of a colorless oil.

Workup

  1. customclose to 20° C
  2. temperatureThe reaction mixture is cooled to a temperature
  3. customclose to 0° C.
  4. customclose to 20° C
  5. waitis continued for 10 min
  6. extractionThe aqueous phase is extracted with dichloromethane
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationthen concentrated
  11. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-0acb4be2807c4427a0359bb9a43dbf8e
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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