Triethylamine → Benzeneethanol, 4-(difluoromethoxy)-, 1-methanesulfonate

HRID 1992388Notes

Reaction equation

HRID 1992388 reaction equation
[F:1][CH:2]([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[F:1][CH:2]([F:13])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][O:12][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 552662382-(4-(Difluoromethoxy)phenyl)ethan-1-ol

Product 1

HCID 54016432Benzeneethanol, 4-(difluoromethoxy)-, 1-methanesulfonateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 2-(4-difluoromethoxyphenyl)-ethanol (0.582 g, 3.09 mmol, from step (iii) above) in methylene chloride (8 mL) was cooled to 0° C. Triethylamine (0.52 mL, 3.7 mmol) was added followed by a solution of methanesulfonyl chloride (0.26 mL, 3.4 mmol) in methylene chloride (2 mL) and the reaction mixture was stirred at 0° C. for 90 min. The reaction mixture was diluted with methylene chloride (40 mL) and the organic phase was washed with water (2×30 mL) and brine (30 mL), dried over Na2SO4, and concentrated in vacuo to give 0.78 g (95%) of the title compound as a colourless oil.

Workup

  1. washthe organic phase was washed with water (2×30 mL) and brine (30 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0211ccf7ff984ec2ab3f4ff1e828cb0c
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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