Water → 2-(2,4,5-Trifluorophenoxy)ethyl methanesulfonate

HRID 1295712Notes

Reaction equation

HRID 1295712 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:18]=[C:17]([F:19])[C:16]([F:20])=[CH:15][C:10]=1[O:11][CH2:12][CH2:13][OH:14].[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>ClCCl>[CH3:21][S:22]([O:14][CH2:13][CH2:12][O:11][C:10]1[CH:15]=[C:16]([F:20])[C:17]([F:19])=[CH:18][C:9]=1[F:8])(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 693650882-(2,4,5-Trifluorophenoxy)ethanol

Product 1

HCID 865916192-(2,4,5-Trifluorophenoxy)ethyl methanesulfonateYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.8 mL, 13.2 mmol) was added to a cold (0° C.) solution of a mixture of the 2-(2,4,5-trifluorophenoxy)ethanol (1.3 g, 6.6 mmol; from Step 3) and methanesulfonyl chloride (0.61 mL, 7.9 mmol) in dichloromethane (40 mL). After being stirred for 1.5 h, water was added and the mixture was concentrated. The residue was dissolved in EtOAc and the solution was washed with 1 M KHSO4, then with brine, dried (Na2SO4) and concentrated to give 1.78 g (quantitative yield) of the title compound as an orange oil. NMR analysis supports the stated structure. This material was used directly in the next step.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washthe solution was washed with 1 M KHSO4
  4. dry with materialwith brine, dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-38a0eec9f1b943ec8b7405b5378da041
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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