Dimethylformamide → 1-(2,6-Dichloro-3-fluorophenyl)ethyl methanesulfonate

HRID 1404578Notes

Reaction equation

HRID 1404578 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([OH:12])[CH3:11].[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C.CN(C=O)C>C(Cl)Cl.O>[CH3:13][S:14]([O:12][CH:10]([C:3]1[C:4]([Cl:9])=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[Cl:1])[CH3:11])(=[O:16])=[O:15]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 167700681-(2,6-Dichloro-3-fluorophenyl)ethan-1-ol

Product 1

HCID 585324961-(2,6-Dichloro-3-fluorophenyl)ethyl methanesulfonateYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1-(2,6-dichloro-3-fluorophenyl)ethanol (5.2 g, 24.9 mmol), methanesulfonyl chloride (6.3 g, 55 mmol, 2.2 eq), and triethylamine (6.1 g) were stirred in 50 ml of DCM and 12 ml of DMF at room temperature overnight. Water and DCM were added, and the layers were separated. The aqueous layer was extracted with DCM. The combined organic layers were dried, evaporated and chromatographed (EtOAc/Hexanes 1:10) to give an oil, 5.11 g, in 71% yield.

Workup

  1. customat room temperature
  2. customovernight
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with DCM
  5. customThe combined organic layers were dried
  6. customevaporated
  7. customchromatographed (EtOAc/Hexanes 1:10)
  8. customto give an oil, 5.11 g

Sources & evidence

ORD record
ord-3b51b375d3ce4411929983ceda3eb78b
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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