Water → HCID 86591618, compound

HRID 1295701Notes

Reaction equation

HRID 1295701 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=1[CH2:15][CH2:16][CH2:17][OH:18].C(N(CC)CC)C.O>ClCCl>[CH3:1][S:2]([O:18][CH2:17][CH2:16][CH2:15][C:8]1[CH:9]=[C:10]([F:14])[C:11]([F:13])=[CH:12][C:7]=1[F:6])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 199916093-(2,4,5-Trifluorophenyl)propan-1-ol

Product 1

HCID 86591618HCID 86591618, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (0.45 g, 3.88 mmol) was added dropwise to a solution of 3-(2,4,5-trifluorophenyl)propan-1-ol (0.46 g, 2.41 mmol; from Step 2) and triethylamine (0.71 g, 7.0 mmol) in dichloromethane (5 mL) at 0° C. The mixture was stirred at room temperature for 2 h. After complete disappearance of the alcohol (HPLC monitoring), dichloromethane (10 mL) and water (10 mL) were added. The aqueous phase was saturated with NaCl and extraction performed. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo to give 0.66 g (100%) of the title compound as a yellow oil. Purity by HPLC: 87%. This material was used directly in the next step.

Workup

  1. extractionThe aqueous phase was saturated with NaCl and extraction
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15a1c5a34cd34330855992608f0d51ce
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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