Methanesulfonyl chloride → HCID 86712574, compound

HRID 1479195Notes

Reaction equation

HRID 1479195 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH2:7][O:8][CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:13]=[CH:12][C:6]([CH2:7][O:8][CH2:9][CH2:10][O:11][S:26]([CH3:25])(=[O:28])=[O:27])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 10536881HCID 10536881, compound

Product 1

HCID 86712574HCID 86712574, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(4-trifluoromethyl-benzyloxy)-ethanol (1.0 g, 4.5 mmol) in dry DCM (20 ml) and DIPEA (2.36 ml, 13.5 mmol), at 0° C., under argon atmosphere, was added methanesulfonyl chloride (421 μl, 5.4 mmol). The reaction mixture was stirred at 0° C. for 10 minutes, then the ice-bath removed and the stirring continued for 2 hours at r.t. The mixture was then diluted with 70 ml of DCM and washed with 50 ml of NaHCO3 saturated solution, 100 ml of water, 100 ml of 2N HCl and 100 ml of water, dried over sodium sulfate and evaporated to dryness affording 1.35 g (yield: quantitative) of methanesulfonic acid 2-(4-trifluoromethyl-benzyloxy)-ethyl ester as a brown oil that was used as such for the next step without further purification.

Workup

  1. customthe ice-bath removed
  2. waitthe stirring continued for 2 hours at r.t
  3. additionThe mixture was then diluted with 70 ml of DCM
  4. washwashed with 50 ml of NaHCO3 saturated solution, 100 ml of water, 100 ml of 2N HCl and 100 ml of water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-fcde2429aeba4410bb6764487229f773
Source dataset
uspto-grants-2016_08
Patent number
US09408850B2

Reaction notes

Loading…